vermont road trip itinerary

The Perfect Vermont Road Trip: One Week Itinerary (2024)

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Vermont is one of few states that you can drive from one end to the other in a day or less, lending itself perfectly to a Vermont road trip! I love how quick and easy it is to get around the Green Mountain State, but Vermont is meant to be explored, with its mountain vistas, winding roads, and the unique businesses that call it home. 

I suggest you take a few days (or better yet, a week or more) and discover all that Vermont has to offer – from well-known attractions to the lesser-known, but certainly not lesser-loved. 

I love Vermont and I have been exploring the state since 2001. In that time I’ve discovered the best spots worth visiting, and I’m sharing those with you today.

Vermont trip itinerary starts in Southern Vermont, but make this excursion your own and start from the north, or begin your journey in central Vermont!

Table of Contents

When is the Best Time to Visit Vermont?

If you’re looking to maximize your bang for your buck during your Vermont road trip, then fall is absolutely the best time to make your road trip to Vermont . There’s nothing quite like a New England road trip, and while you’ll find plenty of lovely things to see and do throughout the rest of the year, fall foliage in this region is unlike anything else and a road trip in Vermont in the fall is the perfect way to see for yourself!

Vermont Road Trip Day One – Bennington 

We recommend starting your Vermont adventure in Bennington , a quaint town located on Vermont’s southern border. Bennington is home to a number of shops, restaurants, and museums. Grab breakfast at Papa Pete’s (home of the giant pancakes!) or the historic Blue Benn Diner . Then, head to Fiddlehead at Four Corners art gallery or Bennington Potters . Spend some time exploring Hawkins House Craftsmarket and satisfy your sweet tooth at Village Chocolate Shop . 

If you are taking your road trip through Vermont from May through October, we recommend making a stop at the Bennington Battle Monument and taking the elevator to the top for panoramic views of three states.

In the afternoon, hit the road on Historic Route 7 to Manchester. Manchester is well-known for its outlets, so plan to spend the afternoon shopping. You don’t want to miss the treasures you find in Manchester’s local offerings though, so a stop at Northshire Bookstore , Manchester Wood , or Perfectpiece consignment shop are a must.

While you’re there, stop at Orvis to feed the trout (or try your hand at fly fishing). Stop by Double Hex or Depot Street Burgers for dinner and rest your head at the Inn at Manchester or one of the other top hotels in the area . If you are taking your VT road trip in summer, a trip up Skyline Drive to Mount Equinox will make your day.

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Vermont Road Trip Day Two – Manchester

The Inn at Manchester makes a great breakfast, or you can climb the stairs of Up for Breakfast , a quaint eatery in the heart of Manchester. After you eat, head to Londonderry and explore Stratton Mountain . At 3,875 feet, Stratton offers unparalleled skiing and riding in southern Vermont and is one of the top ski resorts in the state . In the warmer months, discover Stratton Village that’s home to shops, restaurants, an iconic clock tower, and more. 

In the afternoon, make the trip to Weston – home of The Vermont Country Store . The Vermont Country Store sells Vermont-made products, as well as hard to find toys, trinkets, and treasures. It’s a quintessential Vermont experience, and we guarantee you’ll spend a few hours here. Before dinner, head to Ludlow and get settled into your room for the evening at the Echo Lake Inn , Main + Mountain Motel , or The Pettigrew Inn . For the best bites, get a table at Sam’s Steakhouse or Mr. Darcy’s Bar & Burger . If you’re ahead of schedule, plan to have a little fun at Okemo Mountain Resort . 

Vermont Road Trip Day Three – Plymouth, Woodstock

Wake up early and head to Plymouth, where the 30th President of the United States was born and raised. The Calvin Coolidge Homestead is a National Historic Landmark, featuring an old church, school house, cheese factory, store and post office, barns, walking trails, and more. Coolidge and seven generations of his family are laid to rest in Plymouth. You could spend the whole day here, but we recommend picking up after lunch and heading to Woodstock. 

Woodstock is home to a variety of shops, art galleries, and some of the cutest covered bridges in VT , and is the perfect addition to any trip to New England. Explore its walkable downtown lined with shops or head to Billings Farm & Museum and get face-to-face with horses, cows, sheep, and other animals – small and large. 

There are many incredible inns and hotels in the area , but you won’t go wrong hanging your hat at The Woodstocker B&B , Sleep Woodstock Motel , or 506 on the River Inn . If you’re looking for a luxury place to stay for a romantic New England road trip stop, consider The Woodstock Inn and Resort ; it’s pricy, but the WOW factor is through the roof! For dinner, we recommend Worthy Kitchen and its farm-to-table New American eats, or for a more eclectic menu, The Prince & The Pauper Restaurant .

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Vermont Road Trip Day Four – Montpelier, Waterbury

Rise and shine. Day 4 of your road trip through Vermont starts with a car ride to Montpelier , Vermont’s capital city and one of the best places to live in the state. Stop by our Statehouse and marvel at the building’s gold dome and the Greek Goddess of Agriculture. In the warmer months, tulips and other flowers line the entrance to the capital building, making it even more beautiful. Then head down to The Vermont History Museum . Don’t expect fast food for lunch though. Montpelier is the only state capital without a McDonalds. We suggest saving your appetite until you reach Waterbury, the next stop in your journey. 

Waterbury is a culinary gem and we’re sure there’s not a bad place to eat there. Try The Reservoir , Prohibition Pig , or the ZenBarn . For a super unique VT road trip experience, visit The Blue Stone . The restaurant is home to a vintage well stone resurrected from a farmhouse near Rutland, Vermont. It now serves as a communal bar table and is the perfect spot to share a pizza with friends and family. And of course, no Vermont road trip is complete without a stop at the Ben & Jerry’s Factory . They offer a cool tour that provides an inside-look at how America’s favorite ice cream is made, and the grounds are a fun place for adults and kids alike. Stop by the scoop shop to grab your favorite in a cone. 

Head to Burlington and check in at Hotel Vermont , an independent hotel offering an authentic Vermont experience with Vermont-made products in each room. Rest up; you’ve got a busy day tomorrow. 

Vermont Road Trip Day Five – Burlington

It’s no coincidence that Burlington is affectionately known as the Queen City. It’s up there as one of the coolest places to visit in not only Vermont, but New England. Burlington is a four-season destination, offering a variety of activities for all ages. 

While you’re here:

• Explore Church Street Marketplace and join the 1.5 million visitors that come here annually to shop, eat, and play
• Take your kids to visit ECHO Leahy Center for Lake Champlain , a nature and science museum on the waterfront
• Relax at Waterfront Park, or catch jam band Twiddle’s two-day Tumble Down festival or Grace Potter’s Grand Point North music festival. 
• Get out and swim, kayak, or boat on Lake Champlain, the sixth largest body of water in the United States 
• Ride your bike down the Burlington Bike Path
• Catch a show at the Flynn Center for the Performing Arts , which has hosted the likes of Bob Dylan, Dave Matthews Band, and more.
• Take a hike at one of these top spots around Burlington
• Meander the grounds at Shelburne Museum , its iconic round barn, and its 220-foot steamboat Ticonderoga. 
• Attend a UVM basketball game
• Check out the Burlington brewery scene and eat at some of their top restaurants and coffee shops

Vermont Road Trip Day Six – Stowe

On day 6, you will head to one of the top Vermont destinations: Stowe. This quaint and classic mountain town is a must-visit on any New England road trip itinerary. If you’re into winter sports, the nearby ski resorts will fulfill all your snowy needs. Or if you’d prefer to relax at a luxurious spa, sip craft beers with mountain views, or simply take in the gorgeous scenery, Stowe has all that going on. 

Some of the best things to do in Stowe include: 

• Visiting the Trapp Family Lodge , the resort founded by the real family from The Sound of Music. This property has amazing cross country skiing, an authentic-style bierhaus, and just an all around cozy vibe. It’s utterly Vermonty.
• Riding the bright red gondola to the top of Mount Mansfield, Vermont’s tallest peak.
• Eating at delicious Stowe restaurants’
• Go hike beautiful Stowe!

There are many cool places to stay in Stowe, whether you’re looking for inns, hotels , or vacation rentals , but a stay at Trapp Family Lodge is an incredibly unique Vermont road trip experience!

Vermont Road Trip Day Seven – Continue or End

At this point in your journey, you might decide to keep heading north because there’s so much more to see in Vermont. Or, if your road trip is ending, perhaps it’s time to head south again.

We recommend taking scenic Route 7 south, passing through the towns of Middlebury, Brandon, Rutland , and eventually, reaching Manchester once again. Other suggested Vermont scenic drives can be found here if you want to continue your journey.

Want to make a few more stops?

Middlebury has one of the best downtowns in Vermont, and is also home to the UVM Morgan Horse Farm , the oldest continually-operating Morgan horse breeding programs in the country. Stop by historic Marbleworks and grab a bite at Noonie’s Deli and a new-to-you book at Otter Creek Used Books . 

Brandon has been called “the art and soul of Vermont” and is another must-see downtown, with a number of shops, restaurants, art galleries, and more. Brandon also offers amazing recreational opportunities, including hiking, biking, birding, fishing, and winter sports at Moosalamoo National Recreation Area . 

Whether you have one day or seven, Vermont is your playground. From world-class recreation to unbeatable arts and cultural attractions, there’s something for everyone on a Vermont road trip. Pick your starting point and explore!

Vermont is also great for trips from NYC or trips from Boston , so be sure to consider adding the Green Mountain State to your list of must visit New England road trip vacation destinations!

Explore more of Vermont:

• Most Charming Small Towns in Vermont Not to Miss
• Perfect Spots for a Vermont Weekend Getaway
• Cozy Cabins in Vermont: Perfect for a New England Getaway
• Fun Things to do in Vermont with Kids

Vermont Route 100 Road Trip: our ultimate itinerary (with map)

On this unforgettable road trip through Vermont's Route 100, you'll experience charming towns, breathtaking waterfalls, lakes, forests, cliffs, mountains, and relaxing beaches. Even though you stay within one state, this route has it all. So pack up the car, put on some tunes and get ready for the road trip of a lifetime.

This incredible journey on Vermont Route 100 will take you 200 miles with 4 hours and 40 minutes of driving time. You'll see Vermont's top destinations like Heartwellville, Dover, Ludlow, Pittsfield, Stowe, Troy, Burlington and Lake George.

On your drive, you'll create so many memories, all within one state. Keep reading to learn more about the best routes, places to stay, and top destinations along the way.

Where is Vermont Route 100?

Vermont Route 100 is unsurprisingly located in Vermont and runs from the southern tip of Vermont to the state's northern border with Canada. It's an incredibly scenic and very manageable trip, perfect any time of year and offering a gorgeous travel experience through the adorable towns and forests this state is known for.

The route will pass beautiful towns like Burlington, Stowe, Troy, and many others. You'll get to enjoy nearby parks like Green Mountain National Forest and Mt. Mansfield State Forest.

Where does Vermont Route 100 begin and end?

Vermont Route 100 begins in the beautiful town of Heartwellville, near the border of Massachusetts. Heartwellville is near the popular Dutch Hill Ski Area and scenic Herriman Reservoir.

The end of the route is the northern town of Troy. This delightful town is just a few miles from the Canadian border and is surrounded by natural scenery.

How long is Vermont Route 100, and how long will it take to drive its entire length?

The Entire Length Route will cover 200 miles and only takes place on Vermont Route 100 from the southern end of the state to the north, near the Canadian border. You'll be driving for 4 hours and 40 minutes.

The Round Trip from Burlington Route covers 420 miles of Vermont landscapes. You'll drive for 9 hours and 20 minutes on this incredible loop through the Green Mountain State.

This journey covers a vast amount of territory all within a small state. To get the most out of it, we recommend taking two to three days for the whole length of the scenic road. To get the most out of a slower round-trip drive, it would be best to take four to five days.

Best way to drive on Vermont Route 100

There are two routes that will cover the best of Vermont Route 100 and the gorgeous area that surrounds it. One takes you directly along the route while the longer one takes a different way back on a circular road trip.

The Entire Scenic Route is the best way to explore the stunning Green Mountain National Forest in Vermont, as well as the many charming New England villages and towns that this state is known for.

While you could do part of this route and still get a great experience, part of the charm is getting to see the variety of villages along the way, including Dover, Ludlow and Stowe amongst others.

There are lots of lakes and rivers along the route, such as the Harriman Reservoir at the southern end of the route to the Missisquoi River near Troy near the northern border.

The Round Trip from Burlington Route allows you to drive the entirety of Route 100 but still get to discover a larger city in Vermont like Burlington, which is located on the scenic coast of Lake Champlain.

Another benefit of this round trip is that you can choose whichever direction you'd like to take it. You can choose to descend from Burlington and make your way up Route 100, or descend down Route 100, making your way back to Burlington.

Driving the entire length of Vermont Route 100

Starting in Heartwellville, jump on the famous Vermont Route 100 east. Head past the south shores of the Harriman Reservoir and into the town of Jacksonville.

Continue north and drive to the lovely town of Dover. From here, make your way through the edge of the Green Mountain National Forest.

Drive past the popular Stratton Mountain Ski Resort and continue north to the town of Ludlow. From here, head through the beautiful Coolidge State Forest and into the wonderful town of Pittsfield.

From here, continue on north through some of the most unspoiled forests in America. Soon, you'll pass the striking Moss Glen Falls.

Keep heading north, past the Waterbury Historic District and into the town of Stowe. After spending some time in Stowe, get back on the route and continue on until you hit your destination in Troy.

Driving on Vermont Route 100 on a round trip from Burlington

From Heartwellville, take the epic Vermont Route 100 around the beautiful shores of the Harriman Reservoir. From here drive through the town of Jackson and into Dover, the quiet gateway to the Green Mountain National Forest.

Continue north past the Stratton Mountain Ski Resort and into Ludlow. Head into the Coolidge State Forest and drive on until the town of Pittsfield.

From here, drive north past Moss Glen Falls, Waterbury Historic District, and into the town of Troy. After Troy, head on highway 242 past Jay State Forest.

Drive to the forests and communities of beautiful Lake Champlain. Continue on into the city of Burlington, Vermont's largest city and one of the most vibrant small cities in America.

After exploring Burlington, head back on route and continue south on Route 7, past the western edge of the Green Mountain National Forest, and into the town of Bennington to complete the loop.

Best places to stay along Vermont Route 100

You'll find so much to do and see on this road trip through Vermont. Because of the length of the drive, we've selected two wonderful locations to stop for the night.

A taste of ice cream and nature in Stowe

About halfway on the Entire Scenic Route is the town of Stowe. This wonderful little community is one of the highlights of Vermont Route 100. Stowe is a stunning town known for its beautiful scenery, rich skiing culture and year-round events. There are plenty of highlights to experience in the town.

First, head to Stowe's iconic Main Street. Here you'll experience tons of cute shops, restaurants, and more. You can find all kinds of Vermont products like maple syrup and even wine.

For lovers of ice cream, a must-visit destination is the original Ben & Jerry's factory. Take a tour of where it all began in nearby Waterbury. You'll get to see how B&J's famous ice cream is made, as well as visit an adorable ice cream graveyard for flavors-gone-by.

Once you reach Stowe, we recommend staying at the Trapp Family Lodge . This iconic hotel offers old-world comforts and stunning mountain views.

The hotel is named after the famous Von Trapp family (which manages it), largely fictionalized by the famous film The Sound of Music. It has beautiful Austrian-inspired architecture and European-style accommodations.

There are two swimming pools, a restaurant and a bar to help you relax. There's also free parking, so after your long drive, you can be sure to get right to R&R.

There are tons of skiing trails, local wineries, and scenic hiking paths nearby. You can spend days exploring the nearby trails and quiet streets of Stowe.

Relax and explore the history of Bennington

About halfway along the Round Trip Route is the town of Bennington. This is an ideal stopover on the round-trip route, close to the start of Route 100, so you can rest up before embarking on the stunning drive across Vermont Route 100.

Bennington is mostly known for the Bennington Battle Monument, one of the prominent historic sites in Vermont. It also boasts several museums and art galleries.

There are other beautiful sights to explore but first, explore the Bennington Battle Monument. This 306-foot-high obelisk commemorates the Battle of Bennington during the American Revolutionary war.

From here, head to the Bennington Museum. The museum offers you the perfect opportunity to explore the history of this unique and picturesque town.

When you arrive in Bennington, our top choice for lodging is the luxurious Four Chimneys Inn . Housed in a mansion on an 11-acre property with extensive gardens, this hotel stay is sure to be memorable. The hotel is just over a mile from the center of town and is surrounded by quite natural areas.

Once you're ready to explore, just head outside as the hotel is within walking distance to the Bennington Battle Monument as well as the Bennington Museum. Once you're done sightseeing, there's a garden and on-site bar to enjoy.

Things to see on a road trip on Vermont Route 100

Both routes are full of adventure and fabulous sights along the way. Below we've included our top highlights on the way, so you can make the most out of your journey through Vermont.

The entire length of Vermont Route 100

• Wilmington - Make sure to visit this stunning little village, known as a “shoppers mecca” for it's many quirky stores, delicious restaurants and art galleries.
• Dover - A celebrated skiing spot along Route 100, Dover also offers tons when it comes to small-town charm. Visit one of several museums in this village, or simply spend a couple hours exploring.
• Ludlow - Another unique town along this route, known for nearby Buttermilk Falls as well as many gorgeous mountain and forest trails.
• Pittsfield - There is tons to do in this adorable town, from exploring the Berkshire Museum to enjoying the slopes of the Bousquet Mountain Ski Area.
• Stowe - Stowe is chock-full of attractions, though you might most enjoy walking through the town center and visiting a variety of breweries and restaurants.
• Waterbury - Visit the celebrated Ben & Jerry's factory, where you can get a sneak-peek into this ice cream goliath's world-famous sweet treat recipes.
• Sherbrooke - Located across the border to Canada but well-worth bringing your passport for, Sherbrooke is a stunning city about an hour off your route that boasts gorgeous nature and a celebrated Natural History Museum.

Things to see driving on a round trip from Burlington

• Vermont Teddy Bear Factory - This colorfully painted toy factory near Burlington, Vermont offers informative tours as well as a build-your-own-bear experience.
• New England Maple Museum - Discover the secret behind a delicious bottle of maple syrup at the New England Maple Museum, a popular stopping point along this route.
• Green Mountain National Forest - Take in the beauty of this massive national forest, where you can find dozens of ponds, cliffs and waterfalls that can be reached through several walking trails.
• Lake George - Discover this stunning lake, located across the Vermont-New York State border and boasting beautiful blue waters.
• Saratoga National Park - The site of an unprecedented Revolutionary War victory, the Saratoga National Historical Park offers educational tours of its battlefield and monument. Visit this park for just an extra 30 minutes of travel time.
• Billings Farm and Museum - Thirty minutes off-route find the Billings Farm and Museum. This working farm offers attractions perfect for adults and children alike, including wagon rides, a gift shop, and barns full of farmyard animals.

Best time to drive on Vermont Route 100

Both wonderful routes are traversable any time of the year, though we recommend visiting during the late spring/early summer or during the fall for the best combination of driving conditions and tourist attractions.

Summers in Vermont are warm and quite sunny, with minimal rain. This is generally the busiest season when it comes to tourism, so expect slightly pricier accommodations and busier attractions (especially if you're visiting parks or forests). The temperature in the summer is between 77-82 degrees Fahrenheit.

Vermont Route 100 is well-known for its many winter offerings, so travelers shouldn't worry about not having anything to see or do during the season.

The route's many surrounding forests are arguably at their most beautiful when they are covered with the heavy snow typical of a Vermont winter; just be sure to have chains or winter tires on, and to avoid driving during a winter storm as conditions can get quite bad. The winter temperatures are around 25 degrees Fahrenheit.

Fall is a wonderful time to travel Vermont Route 100, especially if you're driving during the last weeks of September and the first few weeks of October when the leaves begin changing and surrounding foliage takes on warm reds and yellows.

Spring is also a great time to visit, and one of the seasons with a lower tourism rate, so you'll have lots of privacy visiting the many attractions along your route.

There are tons of events happening year-round along route 100, from Christmas and holiday events during the winter months to outdoor events during the summer.

Some highlights include the Vermont Renaissance Faire (Stowe, June), the Stowe Tango Music Festival (August), and the Green Mountain Bluegrass & Roots Festival (Ludlow, Summer).

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Perfect 1 Week Itinerary for a Vermont Road Trip

If you’re yearning for a peaceful escape in New England, look no further than Vermont. This one-week Vermont itinerary offers the perfect road trip through the picturesque and tranquil state.

Vermont’s unspoiled landscapes and breathtaking scenery make it an ideal destination for those seeking solitude and natural beauty. And if you find yourself with extra time, I’ll also provide options to extend your trip and explore more of what Vermont has to offer.

Vermont rolls out an endless supply of quaint Colonial towns filled with white steepled churches, red barns, red covered bridges, and charming inns.

Vermont is heavily forested, with a green canopy that’s set ablaze with fall foliage. If you’re looking to get away from the crowds and fall back into nature and history, Vermont is the perfect place. And, while you’re there, you can enjoy the excellent farm to table cuisine for which Vermont’s renowned.

Here’s my guide spending 7 days in bucolic Vermont. This 200 mile Vermont road trip itinerary takes you from southern Vermont to northern Vermont. You’ll drive through the Green Mountains and weave through charming hamlets.

I point out all the must visit attractions and towns in Vermont. I give you tips for visiting Vermont, including where to hike, where to stay, and where to eat.

I also add some bonus destinations at the end of the one week Vermont itinerary, in case you want to extend your Vermont road trip from 7 days to 10 days or more.

One Week In Vermont Itinerary

This one week in Vermont road trip itinerary takes you from Brattleboro in southern Vermont to Stowe in northern Vermont. Distances between destinations are relatively short, so you won’t feel rushed.

To begin your trip to Vermont, fly into Bradley International Airport in Hartford. Brattleboro is a 1:15 drive from the airport. Or, simply drive to Brattleboro to begin.

Day 1: Brattleboro

Start your 7 day Vermont road trip in the gorgeous town of Brattleboro in southern Vermont. It’s New England’s most supportive art centric enclave. Artists settled in Brattleboro to escape the high rents of New England’s major cities, while still remaining close.

Brattleboro’s downtown has been revitalized. It’s now full of art galleries, upper story artist studios, and a broad array of art venues.

The Brattleboro Museum & Art Center is housed in a restored railroad depot. It presents 8 exhibitions annually.

Brattleboro also has a performing arts scene focused on classical music. The marquis venue is the Marlboro Music School. Brattleboro hosts the New England Bach Festival, a winter Chamber Music Series, and the Vermont Renaissance Festival (in nearby Vernon). Or you can catch a movie at the Art Deco Latchis Theatre.

If nature calls, Brattleboro offers four seasons of sports. You can ski, snowshoe, and skate in the winter. And swim, bike, hike, and golf in the summer. Be sure to check out the Creamery Covered Bridge, a rare surviving example of a 19th century wooden bridge.

Where to stay in Brattleboro : The Inn on Putney Road, Chesterfield Inn, Treehouse Village Inn

Where to eat in Brattleboro : Mocha Joe’s Cafe, Amy’s Bakery Arts Cafe, Peter Havens, Duo, T.J. Buckley’s

Pro tip : If it’s pottery you’re after, head to Putney just 9 miles upriver.

Day 2: Chester, Woodstock & Quechee Gorge

As you leave Brattleboro, head west on Route 9 and link up with Route 100. You’ll be traveling north along the eastern edge of the Green Mountains.

There are plenty of panoramic overlooks to stop and take photographs. And plenty of cute towns to visit along the way — Grafton, Chester, Weston, Woodstock, and Plymouth.

If you have time for just one, I’d pick Chester or Woodstock. Both are enchanting New England villages.

Either makes a good place to overnight, with farm to table eateries and charming inns. Alternatively, you could just visit and continue on to Killington, depending on your agenda.

Chester is best known for its Stone Village and Chester Village Historic Districts. The Stone Village derives its name from the plethora of granite houses in the area.

Chester Village gives off a classic Federal and Colonial aesthetic. Chester is also home to cute boutiques, art galleries, and some fabulous restaurants.

Woodstock is ridiculously charming, the quintessential New England town. Well preserved thanks to the Rockefeller family, strolling the adorable downtown is an activity in and of itself.

There are plenty of boutiques, craft shops, antique stores, and bookstores. FH Gillingham & Sons is a classic Vermont general store. Don’t miss the cute covered bridge.

For some exercise, you can stop for a hike in Quechee Gorge en route to Killington. It’s a fairly easy (but steep) hike down to the base of the gorge.

If the clear water sparkling in the sunshine entices you, there’s a place to enter the river for a swim. The best views are from the bridge. If you didn’t get cheese earlier, now is the time to stock up at the Quechee Gorge Village

Where to stay in Chester : Inn Victoria, Fullerton Inn, Stone Hearth Inn

Where to eat in Chester : Free Range, Heritage Deli & Bakery, Pizza Stone VT

Where to stay in Woodstock : Fan House Bed & Breakfast, Kedron Valley Inn, Twin Farms, The Woodstock Inn and Reort

Where to eat in Woodstock : Barnard Inn Restaurant, Cloudland Farm, Keeper’s Cafe, The Red Rooster

Day 3-4: Killington

One days 3 and 4 of your Vermont itinerary, you arrive in Killington. The town is Vermont’s largest ski resort. It’s a must visit town on your one week in Vermont itinerary.

Killington is really a year round outdoor playground, no matter the season. The downtown is a bit strip mall-ish and overdeveloped. But the views from Killington Peak are sublime.

When the weather is warm, hit the Adventure Center where you can zip line and take scenic lift rides. The ski trails are also open for hiking. Deer Leap Trail is a 3 mile loop and leads to a pretty view overlooking Pico Peak.

In winter, you can ski, snowboard, fat bike, cross country ski, snow tube, and take sleigh rides. Because of its snowmaking capacity, the slopes usually open in early November and the lifts run to early May. The Grand Spa is a nice way to end your day.

Where to stay in Killington : Mountain Top Inn, Birch Ridge Inn, Killington Grand Resort Hotel

Where to eat in Killington : The Garlic, The Peak Lodge, Choices

Day 4-5: Burlington

You may want to spend another day in Killington, if you’re sporty. But, if not, the next stop is Burlington, land of the poet Robert Frost and known as one of the most livable small cities in the US.

In Vermont, there’s a saying that “you can’t throw a stone without hitting a poet/painter/potter.” As the largest town in a state of small hamlets, Burlington has developed a self contained art scene that’s the envy of many.

To some, Burlington is akin to a mini Seattle — a politically and socially progressive enclave of college students, regional power brokers, and creative minds.

The jewel of Burlington’s art scene is the Fleming Museum on the University of Vermont campus. The museum has a wide range of artworks and artists. In June, you can attend the Arts Alive Festival. The Firehouse Center for the Arts also hosts year round exhibitions and art programs.

If you want to see a show, head to the Flynn Performing Arts Center . It’s a fully restored Art Deco masterpiece. The Flynn hosts concerts, plays, and traveling Broadway shows.

If you want to disappear into nature, take the Robert Frost Interpretive Trail. It’s a short 1.2 mile woodland walk. You’ll find signs with commemorative quotes from his poems, including The Road Not Taken .

If you’re a foodie, Burlington will suit. It outshines much of the US with a bounty of locally grown food. Farm to table eating is a well established tradition. There’s even excellent street food at Farmers and Foragers Food Truck.

>>> Click here to book a craft brewery tour

And Burlington has a wonderful farmer’s market on Saturdays in the summer and fall. There’s everything from organic meats and cheeses to flowers and maple syrup.

Local artisans also sell their wares. The market is a must see if you’re visiting in season.

Where to stay in Burlington : Willard Street Inn, Hotel Vermont, The Essex, Made INN Vermont

Where to eat in Burlington : Bleu Northeast Seafood, Hen of the Wood, Juniper, The Great Northern, Honey Road

Day 6: Day Trip To Shelburne and Lake Champlain From Burlington

On day 6 of your 7 day Vermont itinerary, stay in Burlington another night. Then day trip to your next Vermont destination. Drive south to the Magic Hat Brewing Company .

This establishment sparked the growth of Vermont’s microbrewery scene. You can take a free half hour tour and fill up your own growler with an experimental brew.

Just down Route 7 is Shelburne, an affluent suburb of Burlington. Shelburne’s main attraction is the 19th century Shelburne Farms .

There, you can learn how cheese is made from start to finish. Or wander around the beautiful 1400 acre estate. The farm overlooks Lake Champlain. It’s the perfect place for a picnic, if you’re brought your own provisions or purchased some at the farm.

Lake Champlain is one of the most iconic places to visit in Vermont. It’s the 6th largest freshwater lake in the US. First head to Oakland Park.

Admire the beach and, if it’s warm, go paddle boarding. Then hike up the Island Line Trail to the Burlington Earth Clock. The clock is a beautiful large stone circle created by locals called Circles of Peace .

If you want to hit up another microbrewery, the Switchback Brewery is your go to place in Lake Champlain. Then, hike the 2.7 mile long Red Rocks Park Loop Trail, where you’ll have beautiful views of the mountains and lake.

Day 7: Stowe

Just a 30 minute drive from Burlington brings you to lively Stowe Vermont. New England is awash in winter resort towns.

But Vermont’s picturesque Stowe is an incredible year round destination you can’t help but fall in love with. It’s especially known for its breathtaking fall foliage.

En route to Stowe, make the requisite stop at Ben & Jerry’s Ice Cream Factory . You can tour the facilities and get the low down on how their ice cream is made. Afterward, you can taste some limited-release creations.

Then, on to beautiful Stowe. In the winter, Stowe is a popular ski destination, with Vermont’s tallest peak Mt. Mansfield. If there’s snow when you arrive, hit the slopes or take a sleigh ride.

Come summer, Stowe swaps skiing for hiking, golf, mountain biking, kayaking, swimming, and scenic drives up the winding Auto Toll Road. For a magical experience, you can go hot air ballooning over the Green Mountains.

Where mountainous Stowe really shines is its hiking trails, with a range of options to suit every level of experience. Some take you to towering peaks, others end in waterfalls.

The Stowe Pinnacle Trail is a 2.8 mile hike to a breathtaking summit with mountain views. When you’re done hiking, snack on some apple cider donuts or indulge in a Vermont Maple Sugar Body Scrub at the Snowflake Spa .

Stowe also boasts a romantic and picture perfect downtown. Its white steepled church is the focal point. The tiny Main Street is filled with boutiques, art galleries, crafts stores, and antique shops.

Sample some of the finest cheddar cheese and maple syrup in Vermont. There are also libraries, museums, theaters, and cultural organizations to keep your entertained.

Where to stay in Stowe: Stowe Mountain Resort, Trapp Family Lodge. Topnotch Resort

Where to eat in Stowe: Plate, Cliff House, Bistro at Ten Acres

Extra Time On Your Vermont Road Trip?

If you have more than 7 days to spend in Vermont, there are plenty of other places to add to your Vermont itinerary.

1. Montpelier

Add a day in pretty Montpelier, just 38 miles south of Burlington in northern Vermont. Montpelier is the country’s smallest capital, though it feels like a village. Its quirky spirit has earned it the nickname of “Montpeculier.”

Montpelier has a historic little downtown center and vibrant cultural scene, with shops, cinemas, art galleries, etc. But its main claim to fame is as a base for outdoor activities. Hubbard Park offers miles and miles of hiking trails. On its highest peak, a romantic stone tower offers 360 mountain views.

You can also tour the Vermont State House , visit the Vermont History Museum , browse in Kellogg Library, and sample a maple “creemee” at the Morse Farm Maple Sugarworks .

Where to stay in Montpelier : Inn at Montpelier, High Hill Inn

Where to eat in Montpelier : NECI on Main, Sarducci’s, Kismet

2. Manchester

Or, if you’d prefer to hang out in southern Vermont, you can add Manchester to the beginning of your Vermont road trip itinerary. It’s only 1:30 from Brattleboro. Seated at the base of Mt. Equinox, Manchester has been a popular summer resort since the 19th century.

Manchester boasts stately homes and marble sidewalks. Its Main Street could hardly be more picturesque. The town is also a bastion of outlet shopping, with famed upscale factory outlets doing business in cute Colonial buildings.

One must see site in Manchester is Hildene , the summer home of Abraham Lincoln’s son. Hildene is a beautiful Georgian Revival style mansion, which holds some of the Lincoln’s family’s most precious possessions. The property also features beautiful gardens.

For hiking in Manchester, hit the Mt. Equinox Trail . It’s a 6.8 mile loop that’s both steep and challenging. The views from the summit are worth the arduous climb. But you can also access the summit by car at the entrance to Skyline Drive.

Where to stay in Manchester : Equinox, Taconic Hotel, Wilburton Inn

Where to eat in Manchester : Bistro Henry, Mistral’s at Toll Gate, Mystic Cafe & Wine Bar, Ponce Bistro, The Silver Fork

I hope you’ve enjoyed my one week itinerary for Vermont. You may enjoy these other United States travel guides and itineraries:

• 10 Day Itinerary for New Hampshire
• 25 Most Beautiful Town in New England
• 10 Day Itinerary for Coastal Maine
• Fall Foliage Road Trip in New England
• 3 Day Itinerary for Boston
• 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary
• 21 Less Touristy Towns on the East Coast
• Best Art Towns on the East Coast
• Best Art Towns in California

If you’d like to spend one week in Vermont, pin it for later.

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Last Updated on July 9, 2023 by Leslie Livingston

A Perfect Vermont Road Trip Itinerary in 2024

March 18, 2024

Paula Martinelli

Wondering what is the best itinerary for a Vermont road trip?

You have got to the right place! After exploring the whole state, I am here to bring this perfect Vermont road trip itinerary that will take you to the best getaways in Vermont. Vermont is a fun state, and a road trip is the best way to experience it

If you are wondering how many days you need to see Vermont, a good taste of Vermont can be enjoyed in less than a week. This trip involves about 2 or 3 hours of driving daily if you don’t linger. This Vermont road trip itinerary will allow you to see the best parts of the state in 5 days , but longer is recommended if you want to see even more.

I split this Vermont itinerary into five action-packed days, but you could always expand it to have more time in each place. If you prefer slow travel or want to do activities in each town that aren’t on the itinerary, expand each day below into at least two days, for ten or more days exploring this beautiful state.

I’ve packed this Vermont road trip with insider tips that will help you make your experience as memorable as mine. Here you will find the best towns/cities to include and the top sites to see in each one.

You may also enjoy these articles ❤️ :

• 18 Best Things to do in Vermont in winter
• 15 Cozy & Most Romantic Cabins to rent in Vermont
• 15 Best Inns & Boutique Hotels in Vermont

DAY 6 Vermont Itinerary: Manchester

Essential Tips for Your Vermont Road Trip

Before you jump to the best things to do in Vermont, let’s talk about trip planning in Vermont and make sure you are prepared for the best experience.

🏔️ I highly recommend coming to Vermont with a well-defined itinerary of the top things you want to see, visit, and do, in order to maximize your time here.

🏔️ Vermont is a relatively small state, and its north-south distance from the Massachusetts border to the Canadian border is around 159 miles (approximately 256 kilometers). The east-west width varies, with the state being wider in the southern part and narrower in the northern part.

🏔️ Keep in mind that Vermont’s scenic routes and smaller roads may offer slower but more picturesque journeys, and exploring the state’s charming towns and natural beauty along the way can make the trip more enjoyable.

🏔️ Always consider the current road conditions, traffic, and any road closures or detours that may impact your travel time.

🏔️ Make sure you choose accommodation in a good area , where you can easily drive around and explore the main attractions. You can book a cozy cabin in Vermont or you can stay at one of the most beautiful boutique hotels in Vermont.

🏔️ Driving a 4×4 car during wintertime in Vermont is not necessary, but it is nice to have if you are planning to drive outside the town.

🏔️ You can save on your rental car when you book through this site . I use and recommend Discover Cars because it is the most reliable rental car source, and it allows you to compare the prices of different places.

5 Day Vermont Road Trip

Day 1 vermont itinerary: explore brattleboro and overnight in woodstock.

Ready to start your epic Vermont road trip? The first stop is Brattleboro in the southeast corner of VT. Throughout the day, you’ll make your way north to Woodstock , with many fun stops along the way.

🏨 Best Accommodations: I highly recommend the Woodstock Inn & Resort during your nights in Woodstock. It is in downtown Woodstock, and you can walk to some of the places you’ll be visiting today from the inn.🏨

🔎 Must Read: Best Things to do in Woodstock + Complete city guide

1. Explore Brattleboro

Brattleboro sits on the Connecticut River in New Hampshire and is just ten miles north of the Massachusetts border. From the town, there are great views of the river and lots of restaurants. You can also make stops at the Brattleboro Museum & Art Center or the Vermont Center for Photography.

2. Creamery Covered Bridge & Bakery across the street

Less than five minutes west of Brattleboro is the Creamery Covered Bridge. The pedestrian bridge is the only one left in Brattleboro, and it’s over a century and a half old. Make sure you stop at The Vermont Country Deli across the way from the bridge for a tasty pastry or sandwich or to stock up on snacks for the rest of your road trip.

3. Grafton Village Cheese Company

Next on your Vermont road trip is to visit the Grafton Village Cheese Company , which is home to some of the state’s best cheese. All the cheese at the store is handmade in Vermont, using milk from the state. You’ll find cheese, wine, gifts, and more at the store. You can also sample cheeses at the store.

4. Saxtons River Distillery

Just over two miles north of Brattleboro is Saxtons River Distillery . The distillery makes small-batch spirits, many of which are maple based. They produce liqueur, bourbon, gin, and more, all of which are available to try at the distillery. Make sure you have a designated driver if you plan on drinking spirits at the distillery, especially since you have to drive to Woodstock, where you are staying for the night.

5. Spend the Night in Woodstock

Once you are done exploring Brattleboro and enjoying all the fun things to do there, it’s time to head to Woodstock, where you will be staying for the next two nights. Your drive is not too long, with just over 60 miles between Brattleboro and Woodstock.

DAY 2 Vermont Itinerary: Explore Woodstock

Ready for another day of fun? On Day 2 of your Vermont road trip itinerary, you’re staying in Woodstock, where you can enjoy the town, your resort, or the outdoors with lots of fun wintertime activities if you visit during the season.

🏨 Best Accommodations: Another great option for accommodation is   Jackson House Inn  is situated in a fabulous location in Woodstock and rated as exceptional by the guests.

🔎 Must Read: Best Covered Bridges in Vermont

1. Explore Woodstock Downtown

Woodstock is considered  one of the most beautiful cities in America  for a reason. And it won’t disappoint you!

Start by taking a stroll down Main Street in Woodstock, and just get lost admiring the stunning array of buildings of 18th and 19th-century architectural styles. The best streets to mark on your map are The Green, Central Street, and Elm Street to get mesmerized by the beauty of Woodstock.

One of the most classic and beautiful buildings in Woodstock are the Norman Williams Public Library and the Woodstock Inn.

2. Middle-Covered Bridge

Middle Covered Bridge is right across the street from the inn, so it’s the perfect way to start your second day of the Vermont itinerary. The bridge is one of the newer ones, built-in 1969. It was rebuilt after a fire and is open for vehicles and pedestrians.

If you love covered bridges, check out this list of the  20 best-covered bridges in Vermont .

3. Taftsville Covered Bridge

Next on your Vermont itinerary is the Taftsville Covered Bridge, as you won’t want to miss this beautiful site. The bridge is vibrant red and quite long, spanning over the Ottauquechee River. You will have to drive over to this bridge, which is three and a half miles east on US Route 4 from downtown Woodstock.

4. Quechee Gorge

If you continue east from Taftsville Covered Bridge, you’ll reach Quechee Gorge. The gorge is great for a day of hiking, and there are a lot of trails, some of which take you to the bottom of the gorge. The park is beautiful in the fall when all the colorful foliage is blooming, and if you visit when the weather is nice, you can camp at the park.

PRO-TIP: While you are visiting the Quechee village, I recommend stopping for lunch at The Mill, voted one of American’s Most Romantic Restaurants. The food is amazing, cooked with local fresh ingredients, with very creative cuisine, and a stunning backdrop of the Ottauquechee River waterfall and covered bridge. If you are having dinner here I recommend making reservations in advance.

4. Lincoln Inn and Restaurant at the Covered Bridge

The third covered bridge near Woodstock is the Lincoln Covered Bridge. This bridge is in the opposite direction of Woodstock from the Taftsville Covered Bridge. It is just over three miles west on US Route 4.

Next to the bridge is the Lincoln Inn & Restaurant at the Covered Bridge. If the Woodstock Inn & Resort is booked, the inn here is a great alternative for where to stay during your time in Woodstock.

5. Woodstock Nordic Center / Suicide Six Ski Area (Wintertime Itinerary)

I highly recommend the Woodstock Inn & Resort during your nights in Woodstock. It is in downtown Woodstock, and you can walk to some of the places you’ll be visiting today from the inn.

Part of the Woodstock Inn is the Woodstock Nordic Center. You’ll find nearly 28 miles of skating and cross-country skiing trails just south of the main resort. At the center, you can rent snowshoes, fat bikes, winter clothes, and skis to use at the resort.

Another option for outdoor winter activities is the Suicide Six Ski Area, also called the Saskadena Six. The area is north of Woodstock, and you can take one of three ski lifts up the mountain and come down on one of the 24 trails.

PRO-TIP: Don’t forget to check the sky conditions to find out the best ski areas.

6. Ice Skating at Union Arena

Another fun winter activity in Woodstock is ice skating at Union Arena. The arena is just west of downtown Woodstock. You can ice skate here during public skate hours, and they have ice skates available to rent.

DAY 3 Vermont Itinerary: Explore Mad River Valley – Waitsfield/Warren

I hope you had a fun day in Woodstock, but now it’s time to head further north and explore the Mad River Valley. Today you’ll see more covered bridges and two small towns before heading to Stowe for the night. 

🏨 Best Accommodations: 1824 House Inn + Barn is a perfect accommodation located in Waitsfield offering many things to do such as hiking, cycling and golf. Or I recommend the Mad River Lodge also located in Waitsfield offering very comfortable accommodation. 🔎 Must Read: 10 Best Vacation Gateway in Vermont

1. Go on the 7 Covered Bridges Loop

As you already know, after day 2, Vermont has some amazing, covered bridges. Today, explore even more of them during a drive around the 7 Covered Bridges Loop .

The loop is 40 miles roundtrip, and if you spend time enjoying each bridge, it should take about half a day or so. Learn more about the Covered Bridge Loop .

During your stops at the Waitsfield Covered Bridge and the Warren Covered Bridge, stay to explore the towns and see the other sites today.

2. Waitsfield Historic Center

The Waitsfield Historic Center makes up the small town of Waitsfield. It was established in the early 19th century as a commercial hub for the farmers in the area. Be sure to stop by the Waitsfield Historical Society to explore the town’s history and get more information about events in Mad River Valley.

Waitsfield is also a great place to stop and shop, which is fitting since it was originally built as a commercial town. There are a variety of shops, including craft stores, art galleries, boutiques, a bookstore, and gift shops.

3. Warren Historic District/Warren General Store

The other place you have to stop along the Covered Bridge Loop is the Warren Historic District. The Warren Covered Bridge is in the historic town, as are many old buildings built in the 1800s. The town is on the National Register of Historic Places since it was an important mill town thanks to its location on the Mad River.

In the historic district is the Warren General Store . The store has a deli and a bakery where you can get fresh food and treats. They also have a big selection of craft beer, wine, fashion, and unique toys and gifts.

4. Warren Waterfall

South of the Warren Covered Bridge is Warren Falls. The waterfall flows into a natural swimming hole. Bring your swimsuit and jump off the cliffs around the hole if you visit in the summer.

DAY 4 Vermont Itinerary: Explore Stowe and Waterbury / Overnight in Stowe

After exploring Mad River Valley, you’ll spend a night or two in Stowe, VT . Stowe is one of the most popular places in Vermont, thanks to its famous ice cream factory and tall mountain and ski resort.

🏨 Best Accommodations: 1860 House Inn  is set in a historic building and offers an old-style charm! The property is situated close to the center of Stowe village too so there are plenty of restaurants and shopping opportunities nearby. 🔎 Must Read: Best things to do in Stowe + Complete city guide

1. Explore Stowe Downtown

Stowe’s covered bridge is the Gold Brook Covered Bridge. The bridge is haunted by a girl named Emily, who died at the bridge, which is why it is also sometimes called Emily’s Bridge.

From the bridge, head into town and visit Stowe Church, one of the most picturesque churches in the state, with a beautiful mountain view behind it.

2. Take the Cable car to Mount Mansfield

Even if you are not staying at the resort, you should take the cable car up the mountain. The views are amazing from the gondola, which runs in the summer. At the top of the mountain, the highest in the state, are hiking trails and a restaurant.

3. Visit the Classic Trapp Family Lodge

The Trapp Family Lodge is a historic lodge between the mountain resort and downtown Stowe. The lodge is close to the ski slopes and has an indoor pool, a hot tub, tennis courts, outdoor trails, and on-site dining.

PRO-TIP: One of the best accommodations options is the famous  Trapp Family Lodge : This is one of the main attractions in Stowe and for a reason.

4. Ben & Jerry’s Factory

Finally, no matter how long you spend in Vermont, one of the places you cannot miss is the Ben & Jerry’s Factory . The factory is in Waterbury and is the only one open for the public to see. You can tour the factory and try the classic and newest ice cream flavors.

It makes a great short drive to visit the factory and try some of the amazing flavors, visit the gift shop and have some fun visiting the flavor graveyard where you can find all the retired flavors over the years.

DAY 5 Vermont Itinerary: Burlington and Shelburne

Day 5 of your Vermont road trip itinerary will allow you to spend the day in the small towns of Burlington and Shelburne, which are right next to each other. 

If you have more than five days in Vermont, I highly recommend spending a few more days in Burlington. You can slow down and spend more time at each of these sites.

🏨 Best Accommodations:   Williston Village In is in a great location and offers an escape from the hustle and bustle of everyday life. It’s also half the price of some of the other hotel chains in the area. 🔎 Must Read: Best Things to do in Burlington + Complete City Guide

1. Church Street Marketplace

Church Street is one of the main streets in downtown Burlington . The Marketplace, an outdoor mall, is one of the main attractions.

The marketplace has places to shop, eat, and entertain. The surrounding blocks have even more places, so you could spend a good part of your day here.

2. College Street

College Street is one of the other main streets in Burlington which runs perpendicular to Church Street. The street has great restaurants and coffee shops. It runs west to Lake Champlain, so it’s a good street to walk down if you are heading to the lake.

3. Visit the Shelburne Museum

The final stop today is in Shelburne, just south of Burlington. The Shelburne Museum is home to over 100,000 pieces of folk art. The museum spans multiple buildings and on the site is a toy shop, multiple art galleries, and a covered bridge.

4. Lake Champlain

Burlington sits on Lake Champlain. You can enjoy the lake from the Waterfront Park or at one of the many lake-side restaurants. Or, you can rent a boat or a kayak and see Burlington from the water.

The final day of your Vermont road trip itinerary is going to be a lot of fun! It’s time to head back down south to Manchester in Southwest Vermont. The drive from Burlington to Manchester is 100 miles and by the end of the day, you’ll have looped around the whole state in less than a week.

🏨 Best Accommodations: The Inn at Manchester  is set on four acres of landscaped gardens so there’s plenty of room to explore. You’ll also be close to Manchester town center which has lots of charming restaurants and shopping opportunities. 🔎 Must Read: 18 Awesome Things to do in Vermont in Winter

1. Hildene House

Start the last day of your Vermont itinerary by visiting the Hildene House the home to Robert Lincoln, son of President Abraham Lincoln. The home sits on 412 acres and has tours, educational exhibits, and hiking trails.

There are also seasonal events like Christmas decor in the winter and peony season from late May to June in the gardens. On the home’s farm, there are animals to visit and a cheesemaking area.

2. Mount Equinox

Your final stop, and one of the prettiest, is Mount Equinox Skyline Drive. The paved road takes you through 5.2 miles of mountains up to the top of Mount Equinox. Along the drive, there are many lookouts and picnic areas to stop at and enjoy the views.

Then, at the top, you’ll get the best views from the 3,848-foot summit where there are picnic areas and a visitors center to end your day.

PRO-TIP: The drive is open from Memorial Day weekend through October. Make sure to visit when the weather is clear so you can see all the mountain views.

Vermont Road Trip | Trip Resources

Planning a road trip in vermont.

If you are going on a road trip to Vermont, pre-planning, researching, and understanding what you are looking for in a destination will help make your travels far more successful and safe.

Here is some further information I think you might need to plan your Vermont itinerary. Make sure you check the following too:

15 Incredible Cabins you can Rent in Vermont 15 Best inns & boutique hotels in Vermont Winter Vacation in Vermont: 10 Perfect Winter Getaways! 13 Awesome Things to do in Stowe in winter 15 Terrific Things to do in Burlington in winter 20 Amazing Things to do in Woodstock, VT 18 Awesome Things to do in Vermont in Winter

Best Accommodations in Vermont

When planning your Vermont Road Trip, m ake sure you choose accommodation in a good area , where you can easily drive around and explore the main attractions.

Making your reservations in advance is also part of a well-planned visit, as depending on what time of the year you are visiting Vermont it may be hard to find last-minute accommodations.

For an even more authentic experience, consider booking a cozy cabin in Vermont or you can stay at one of the most beautiful boutique hotels in Vermont.

Driving tips for your Vermont road trip

If you are taking a road trip during winter time, a 4×4 car is not necessary, but it is nice to have if you are planning to drive outside the town.

Lastly, if you need to rent a car for your Vermont road trip . You can get 15% off your rental car when you book through this site . I use and recommend Discover Cars because it is the most reliable rental car source, and it allows you to compare the prices of different places.

What is the Best Time To Visit Vermont?

FALL: It is the most popular time of the year to visit Woodstock because it is when the fall foliage changes from early October to around the third week of the month. It is important to plan in advance, especially make your accommodations in Vermont well in advance. Prices for hotels and flights will be the most expensive during these months.

WINTER: The fact is that the whole state of Vermont is cold in winter – with temperatures that can drop below zero. But as long as you pack accordingly, you will love it because the snow makes Vermont’s landscape look and feel even more spectacular! Make sure to check the weather , and have fun on the snow slopes around Woodstock!

SUMMER: During summer time Woodstock offers great outdoor eateries, swimming holes, and a great brewery to enjoy the outdoors. The warmest time of year is generally mid-July where highs are regularly around 84.9°F (29.4°C) with temperatures rarely dropping below 59.5°F (15.3°C) at night.

SPRING: Spring is a beautiful time to visit Woodstock, plus it is a perfect time to visit for a quiet and peaceful getaway. There are many things to do outdoors that will allow you to enjoy, such as the maple syrup flowing, enjoying the spring wildflowers, and drinking a local beer sitting outside around a fire pit.

What to Pack for your Vermont Road Trip?

Make sure you are prepared, considering the season and the activities you are planning to do. Here are some quick tips:

• Pack layers of clothes so you can be comfortable in the changing temperatures!
• Bring a pair of jeans and a light sweater to wear in the evenings
• Pack rain gear – you don’t want to get soaking wet while exploring
• A hat, gloves, and scarf  can’t go wrong, even in summer.
• If visiting in winter, bring good quality sturdy snow boots .
• Bring warm leggings to wear as a layer is a smart choice!
• Pack a good jacket, check my complete review guide on the Top Jackets for Travel
• If you are planning to carry a backpack for your trip to Vermont, I have compiled a very detailed review of the Best Backpacks for Travel on the market today

PACK SMART ALERT!

If you are planning to carry a backpack for your trip to Alaska, I have compiled a very detailed review of the Best Backpacks for Travel in the market today – Also, I recommend bringing a good and warm jacket waterproof jacket for your trip, check my complete review guide on the Top Jackets for Travel – Bring some warm pants, you can check the best Warm leggings in the market – especially because they are a great option for layers too.

Vermont Road Trip Conclusion

I hope you have enjoyed this Vermont road trip itinerary!

Vermont is a fun state, and a road trip is the best way to experience it. A 5-day road trip will allow you to see the best parts, but even longer is recommended if you want to see and do more, such as visit all the 10 best gateways in Vermont .

This Vermont itinerary includes the bigger cities of Montpelier, the state capital, and Manchester, but also, will take you to the best towns while experiencing covered bridges, and amazing farm-to-table fresh food.

If you have any questions, leave a comment below and I will be happy to help!

You may also enjoy reading:

• 15 Incredible Cabins you can Rent in Vermont
• 15 Best inns & boutique hotels in Vermont
• Winter Vacation in Vermont: 10 Perfect Winter Getaways!
• 13 Awesome Things to do in Stowe in winter
• 15 Terrific Things to do in Burlington in winter
• 20 Amazing Things to do in Woodstock, VT
• 18 Awesome Things to do in Vermont in Winter
• 30 Dream Destinations for your Bucket List!

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Winter Vacation in Vermont: 10 Best Vermont Winter Getaways

20 Awesome Things To Do in Woodstock, Vermont in 2024

20 Awesome Things to do in Vermont in Winter of 2024

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23 Scenic Stops on a Route 100 Vermont Road Trip Itinerary

A Route 100 Vermont road trip is often considered one of the most scenic drives in the Green Mountain state and the prettiest fall foliage road trips in New England. At just over 200 miles, Vermont’s Route 100 meanders through small towns, follows the path of winding rivers, and travels past both ski resorts and splashy waterfalls.

You can travel this route in just over five hours, but to fully enjoy this scenic drive, you will want to spread it out over a long weekend or more. This scenic Route 100 road trip itinerary will introduce you to what makes Vermont so special with stops at maple sugar houses , craft breweries , country stores , cheese makers , historic sites , gorgeous waterfalls , and charming Vermont villages .

Growing up, I spent all of my family vacations in Vermont, taking day trips and scenic drives throughout the state. More recently, I have driven this route many times in the last couple of years on various trips to Vermont. After exploring all of its nooks and crannies, I’m excited to share some of my favorite stops along the beautiful Route 100 Scenic Byway.

Vermont Route 100 Road Trip Stops

Note: This post may contain affiliate links. If you click a link and make a purchase, I may receive a small commission. All opinions are my own.

This Vermont Route 100 road trip itinerary covers the section from Wilmington, in Southern Vermont, up to Stowe. While Route 100 continues up into the Northeast Kingdom, the section covered here is the most popular and you can easily extend your trip or take a day trip from a home base in Stowe if you want to explore further.

Vermont Route 100 Route Trip Map

This map was created using Google My Maps and covers your Route 100 road trip and the stops suggested below. You can click on the star next to the title and save this to your Google Maps account or click on the share icon to send it to yourself via email. Click on any of the icons to learn more about that destination or attraction.

Wilmington, Vermont

Wilmington is located on the Molly Stark Byway, halfway between artsy Brattleboro and historic Bennington in Southern Vermont. Located near the base of the Scenic Route 100 Byway, this charming town makes a perfect starting point for your road trip itinerary.

The Wilmington Village Historic District is on the National Register of Historic Places with a number of well-preserved 18th- and 19th-century buildings. Downtown you will find a statue of Molly Stark, a local figure made famous by her husband, General John Stark, a Continental general of the American Revolution, who famously gave the battle call of “There are your enemies, the Red Coats and the Tories. They are ours, or this night Molly Stark sleeps a widow!” before engaging with the British and Hessian army in the Battle of Bennington.

In downtown Wilmington, you will find gift shops, boutiques, cafes, and independent book seller Bartleby’s Books. For a simple meal, try the old-school diner vibe of local favorite Dot’s, or the Village Roost is a trendier coffee shop and cafe in the heart of downtown.

Be sure to take a walk across Reardon’s Crossing bridge for lovely views of the Deerfield River. In the summer, you can also explore the shores of Lake Whitingham and in the winter, you will find skiing nearby at the private Hermitage Club at Haystack Mountain or Mount Snow a bit further north.

If you want to stay overnight before starting this road trip, The Vermont House is located right in downtown, and the White House Inn is very close by.

Mount Snow, Dover or Okemo, Ludlow

As you head north on Route 100, you will know you are near the ski resorts when instead of barns beside the road, you start to see ski shops and restaurants. If you get hungry, you can stop for some wood-fired pizza at American Flatbread , a popular New England chain. Sticky Fingers Bakery is the place to go for homemade cinnamon rolls, croissants, danish, cookies, breads, and more.

You can easily pass these right by, but if you are splitting your trip up over multiple days, you might want to make time for a stop at either Mount Snow in Dover (15 minutes north of Wilmington) or Okemo , further north in Ludlow. Luckily, these are both located right off of Route 100 and offer great skiing and winter snow sports in the winter, but in the summer or select days during leaf peeping season you can still enjoy hiking, mountain biking, or scenic chairlifts.

If you hold out until you get to Okemo, you can also enjoy additional activities such as the Timber Ripper Mountain Coaster, Haulback Ropes Challenge Course, Coleman Brook Mining Company, or Lumberin’ Cal Miniature Golf. Winter also brings ice skating, snow tubing, snow shoeing, or fat biking.

Jamaica State Park & Hamilton Falls, Jamaica

As you head north on Route 100 from Dover, you will pass through the outskirts of the Green Mountain National Forest. This scenic stretch of road is some of the prettiest, especially when it follows the course of the West River, cascading over the rocky river bed. If you want to stretch your legs and enjoy nature, make a stop at Jamaica State Park (30 minutes north of Dover.) Before you get there, you may want to stop at the Scott Covered Bridge .

From the campground, it is a three-mile (one-way) hike to Hamilton Falls , one of Vermont’s largest waterfalls. Here Cobb Brook cascades 125 feet down a mountain slope, through a woodland, and into a series of large potholes. There are several falls here, one of which drops 40 to 50 feet into a large pool. While this is a popular swimming spot, it is also quite dangerous and many have lost their lives so I wouldn’t risk it.

Jamaica State Park is located at 48 Salmon Hole Ln, Jamaica, VT 05343

If a hike makes you hungry, 10 minutes further up the road you should stop at Honeypie , a local fast food restaurant specializing in burgers, sausages, sandwiches, and milkshakes from the couple behind James-Beard nominated SoLo Farm and Table. You can also pick up some local Vermont beers at Meulemans’ Craft Draughts across the street. If you just want something sweet, stop at Grandma Miller’s Pies and Pastries instead.

Honeypie is located at 8811 VT-30, Jamaica, VT 05343. Meulemans’ Craft Draughts is located at 8814 VT-30, Rawsonville, VT 05155. Grandma Miller’s Pies and Pastries is located at 52 Hearthstone Ln, South Londonderry, VT 05155

Taylor Farm, Londonderry

When you get to Londonderry, take a short side trip on Route 11 to Taylor Farm . The farm store features a variety of local and artisanal products including an extensive selection of Vermont cheeses, homemade bread, Vermont maple syrup, jams, and handcrafts.

Each season brings something new to Taylor Farm. Summer brings concerts, animal visits, lawn games, and maybe even a wagon ride. In the fall, the farm is bursting with farm-grown apples and pumpkins and in the winter, Taylor Farm offers sleigh rides. These 45-minute rides travel through the fields and into the woods to a fire and warming hut where you can enjoy some hot cider.

If you really want to break up your drive, take a day to enjoy nearby Manchester and stay overnight at one of the village’s many charming inns and hotels.

Taylor Farm is located at 825 VT-11, Londonderry, VT 05148

Vermont Country Store, Weston

From Londonderry, it is only 10 minutes further up Route 100 to Weston and the Vermont Country Store . Established in 1946 by the Orton family, this iconic spot is like visiting the L.L. Bean of Vermont. You will find a huge array of Vermont-made products including clothing and housewares, along with food products.

This is a spot to buy Vermont maple syrup, Vermont cheeses, jams, and other specialty products. It is fun to wander the wood-planked rooms to discover what treats await…like hard candy sticks and old-fashioned hard candies and fudge.

The Vermont Country Store also has a snack bar and cafe, along with picnic tables. So pick up a treat, grab a rocking chair on the porch, and travel back in time at this quintessential country store.

The Vermont Country Store is located at 657 Main St, Weston, VT 05161

Buttermilk Falls, Ludlow

Just north of Okemo Mountain Resort, 20 minutes north of Weston, turn left onto Route 103 to Buttermilk Falls . You can access the falls via a short walk. While it is a popular swimming spot in the summer, it is especially beautiful in the fall.

Green Mountain Sugarhouse

Back on Route 100, it is only a couple of minutes further to Green Mountain Sugarhouse . This red-roofed sugarhouse overlooks the beautiful Lake Pauline so order a maple creemee (maple-flavored soft ice cream) and grab a seat on an Adirondack chair to enjoy the view. They make and sell everything from maple syrup to maple fudge, and it is also a Vermont country gift shop (albeit much smaller than the Vermont Country Store.)

Green Mountain Sugarhouse is located at 820 Route 100 N, Ludlow, VT 05149

Calvin Coolidge Historic Site

When you get to Plymouth Notch, take a side trip up Route 100A towards Bridgewater for a visit to the President Calvin Coolidge Historic Site . Also known as the Coolidge Homestead, this was the childhood home of the 30th president of the United States and the place where he first took the presidential oath of office.

Visitors can see the Coolidge Birthplace, Coolidge Homestead, Union Christian Church, Schoolhouse, and Plymouth Cemetery, along with permanent exhibits and enjoy the nature trails throughout the grounds.

Calvin Coolidge Historic Site is located at 3780 VT-100A, Plymouth, VT 05056

Plymouth Artisan Cheese

Plymouth Artisan Cheese is home to America’s oldest cheddar, made from the original 1890 Vermont recipe. The Plymouth Cheese Factory was built in 1890 by Colonel John Coolidge, a dairy farmer who was looking to extend the shelf life of his milk. Today, the company makes multiple flavors of cheddar including Farmer Fred’s Favorite, black truffle, sage and herb, hot pepper, and cheese curds. The shop is open 11 – 4 everyday, keep that in mind because somehow I always seem to get there minutes after they close!

Plymouth Artisan Cheese is located at 106 Messer Hill Rd, Plymouth, VT 05056

Killington, Vermont

Killington is the perfect halfway point on your Route 100 Vermont road trip to stop for the night, as there are so many options for places to stay (although it will be pricier during ski season.) I’ve stayed at The Mountain Inn in Killington. It is a newly renovated hotel that sits on top of a distillery and restaurant. It wasn’t fancy but it had modern decor and a fun vibe (and good price!)

Find more places to stay in Killington:

Long Trail Brewing Co.

Brewing since 1989, Long Trail Brewing Co. is one of Vermont’s early craft brewers, specializing in German-style beer. I first visited Long Trail in the early 1990s, but today you can eat and drink at its spacious riverside pub and restaurant, which was inspired by the Hofbräu House in Munich, Germany. You can either continue up Route 100A to Long Trail for a drink before checking in to your hotel at Killington, or go back out for dinner.

Long Trail Brewing Co. is located at 5520 US Rte. 4, Bridgewater Corners, Vermont 05035

Thundering Brook Falls, Killington

Start off your day with a short hike to Thundering Falls , which is said to be the sixth tallest waterfall in Vermont. Start at the River Road parking area and follow a boardwalk over the Ottauquechee River and through the open Ottauquechee River floodplain. The trail then ascends to a viewing platform overlooking the Falls via an accessible switchback and spur trail.

Thundering Brook Falls is located at 2295 River Rd Fork, Killington, VT 05751

Rochester Country Store, Rochester

Thirty minutes north of Killington you will come across the small town of Rochester, home to the Rochester Cafe and Country Store . This homey cafe has been serving up breakfast, brunch and lunch favorites for over 30 years. Even if you aren’t hungry yet, the quaint country store is filled gifts and local goodies. It is also a good spot to pick up a picnic for your next stop!

The Rochester Cafe and Country Store is located at 55 N Main St, Rochester, VT 05767

Texas Falls Recreation Area, Hancock

It is only 10 minutes from Rochester to the Texas Falls Recreation Area , but there isn’t cell service in the area, so be sure to map it in advance. You will need to turn off Route 100 at Route 125 West to reach the falls. This area features a one-mile nature hike through the woods, but you don’t even need to do that to see the stunning waterfalls that have been carved through the rock over the generations. The best views are right at the beginning of the hike, just past the bridge that connects the trail to the parking lot. 

Moss Glen Falls, Granville

Head back to Route 100 North and continue 15 minutes further to Moss Glen Falls , a pretty 30-foot waterfall. The Falls are located on the west side of Route 100, so the parking lot is easier to access from the southbound side. When traveling north, you will need to keep your eyes peeled or you will miss it.

Warren Falls, Warren

Another 10 minutes further north, you will come to Warren Falls . This is a series of waterfalls, rather than a tall and more dramatic waterfall like Moss Glen Falls, however, it is still a beautiful spot to stop if you love waterfalls. If you have already had your fill, feel free to skip this spot. The parking lot can get a little crowded on a busy day because this is a popular spot for families, picnickers, and hikers. But a short walk towards the cascades will bring you to a beautiful view of the water rushing through rocks. Stake out a spot on the rocks and sit and enjoy a picnic or just take in the view.

A bit further north brings you to the Warren Store , a former stagecoach inn and boarding house that is now a charming general store.

Warren Falls is located at 3919 Vermont Rte 100, Warren, VT 05674

Lawson’s Finest Taproom, Waitsfield

The cute, artsy town of Waitsfield , near Mad River Glen Ski Area, is the beginning of the Mad River Scenic Byway. This is a great spot to stop for lunch, or even stay the night if you have more time for your Vermont road trip itinerary. You will find art galleries as well as pottery and glass artisans. You can grab lunch at the Three Mountain Cafe, American Flatbread, or Mad Taco, or treat yourself to a maple ice cream cone at Canteen Creemee. 

Waitsfield is also home to Mad River Distillers and a few craft breweries, including one of my husband’s favorites, Lawson’s Finest Liquids . The taproom serves up tasting flights and light bites and is a must stop for New England IPA lovers.

Lawson’s Finest is located at 155 Carroll Road, Waitsfield, VT 05673

Waterbury, Vermont

Waterbury also offers plenty of options for lunch or dinner, including Prohibition Pig or  Maxi’s , a local favorite for breakfast and brunch. If you stick around for dinner, try to get a reservation at Hen of the Wood . I’ve eaten at their location in Burlington and this farm-to-table restaurant is fabulous.

Ben & Jerry’s Factory, Waterbury

Ben & Jerry’s Factory is one of the most popular attractions in Vermont and a must visit for ice cream fans. You can take a 30-minute guided tour through Ben & Jerry’s first factory. Built in 1985, this factory continues to manufacture upwards of 350,000 pints per day and you may get lucky to see the production in action during the tour. The tour ends in the Flavor Room with a tasting of one of the famous flavors.

Even if you don’t take a tour, you can still visit the small Scoop shop and retail area. One thing you do NOT want to miss is a stroll through the Flavor Graveyard. I know it sounds a little creepy, but it is actually quite fun to see all the flavors that have been “de-pinted.” Just keep in mind that tour tickets are released two weeks in advance and pre-purchasing is highly encouraged.  

Ben & Jerry’s Factory is located at 1281 Waterbury-Stowe Rd Route 100, Waterbury Village Historic District, VT 05676

Cabot Creamery, Waterbury

Any cheddar cheese fan will want to make a stop at the Cabot Creamery Store in Waterbury, just up the road from Ben & Jerry’s. In addition to a selection of delicious cheeses, the store sells many other Vermont specialty foods including maple products, Vermont microbrews, and hard ciders. While you are there, grab some extra creamy sea salted butter to spread on freshly baked bread. 

Cabot Creamery is located at 2657 Waterbury-Stowe Rd, Waterbury Center, VT 05677

Lake Champlain Chocolates, Waterbury

Located right next door to Cabot Creamery is the Waterbury location of Lake Champlain Chocolates . Not only is this a chocolate shop, but it is also a chocolate cafe offering hot chocolate, coffee, and ice cream. I’ve visited the main Lake Champlain Chocolate store in Burlington and I was so impressed with the quality and ethical-sourcing offered by this family run company. You can also grab some factory seconds for a steal!

Lake Champlain Chocolates is located at 2653 Waterbury-Stowe Rd, Waterbury, VT 05676

Cold Hollow Cider Mill

Just thinking about the freshly cooked apple cider donuts from Cold Hollow Cider Mill makes me hungry! I’d suggest starting at the hard cider tasting room. When I visited, if you purchased a tasting flight you got a coupon for six free donuts next door. After your tasting, visit the main store for apple cider, apple cider donuts, and a wide selection of Vermont products.

The restaurant also serves breakfast and lunch with breakfast sandwiches on homemade cheddar cheese biscuits, wraps, fresh salads, our homemade soups, grilled Paninis, and sandwiches served on homemade white or sweet potato bread.

Cold Hollow Cider Mill is located at 3600 Waterbury-Stowe Rd, Waterbury Center, VT 05677

Stowe, Vermont

I’d suggest finishing up your Route 100 road trip in the ski town of Stowe. There are many places to stay nearby that offer a great selection of outdoor mountain activities including Topnotch Resort , Stoweflake Lodge , and the Trapp Family Lodge . The Bench in Stowe is a great spot for lunch or dinner.

From Stowe, you can enjoy hiking and outdoor summer or winter activities at Stowe Mountain Resort. You can also take day trips to shop at the Vermont Flannel Store and Johnson Woolen Mills in Johnson

Find more places to stay in Stowe:

Vermont Route 100 Road Trip Tips

If you are driving an electric vehicle, you will want to be strategic about where and when you charge. While Vermont has the highest per capita rate of public charging availability in the United States, you need to know where to look . There is a large bank of Tesla super chargers in Brattleboro, which you could use to charge before starting out. You will also find chargers in Wilmington, Ludlow, Killington, Rochester, Warren, Waitsfield, Waterbury, and Stowe, along the route.

Gas powered cars should also keep an eye on the fuel gauge when driving the scenic byways of Vermont, but you will find gas stations in small towns along the way. Just keep in mind that some may have limited hours.

Drive South to North

It really doesn’t matter which direction you drive Vermont’s Route 100, but unless you are flying into Burlington, I think it is more fun to drive the scenic route north and then take the highway back south. Plus, if you start in Wilmington, you are closer to more airports if you are flying in (3 hours from Boston, 1.5 hours from Hartford CT, 2 hours from Manchester NH, and 1.5 hours from Albany NY.)

Be Weather & Traffic Ready

Route 100 is known as the “Skier’s Highway” since there are so many ski resorts located on or near the scenic byway including Mount Snow, Okemo, Stratton, Killington, Pico, Mad River Glen, Stowe, and others. If you are taking this trip in the winter, be prepared for crowds and for snow. Make sure you have good all-weather tires (or consider snow tires) and bring along an ice scraper and portable snow shovel. Twice I’ve gone on a ski trip and had to shovel out my car with my hands so don’t make my mistake!

Plan Early for Leaf Peeping

In the autumn, leaf peepers line the scenic byways of Vermont and crowd the small trail parking lots and attractions. If you want to visit during prime fall foliage season, you need to book your accommodations in advance! Peak foliage times vary but typically the last week of September through Columbus Day Weekend / Indigenous People’s Day is the busiest. You should use a fall foliage tracker to follow the color change progress each year.

Bring a Map

Many portions of Route 100 do not have cell service so it helps to bring along a paper map, which you can pick up at a Vermont visitor center or many country stores and attractions. If you don’t have a map, be sure to map out your route, with the stops, before you leave WiFi or cell service. Technically you don’t need a map if you stick to Route 100, but it does take a few twists and turns, and there are a few stops that are slightly off the route that are still worthy of a stop.

VISITING VERMONT? YOU MAY BE INTERESTED IN…

• Things to do in Burlington, Vermont
• Things to do in Manchester, Vermont
• Basin Harbor Resort on Lake Champlain
• Glamping in Vermont at Highwood Retreat
• 17 Stops on a Vermont Road Trip
• 20+ Spots to go Glamping in New England
• Best fall getaways in New England
• Things to do in the White Mountains, New Hampshire

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: October 6, 2023

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Where to See Fall Foliage

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Scenic Road Trips

The 8 Best Vermont Road Trips

In Vermont, road-tripping is as exhilarating as any outdoor sport. This land of mountains, maples, covered bridges, and cows never disappoints drivers with its bending, ascending roads and rustic scenes. And if you're in the passenger seat, even better: You can scout angles for panoramic photos and keep an eye out for farm stands, funky shops, and roadside oddities like Vermontasaurus. Because cell phone service is still spotty in some parts of Vermont, it's always wise to have a game plan before you hit the road. Here are eight outings that showcase Vermont's splendid scenery and its singular way of life.

Vermont Route 100

Just drive the Scenic Route 100 Byway—south to north or north to south—and you can travel nearly the entire length of the state. It's an easy-peasy road trip chock full of quintessential Vermont experiences. Plan to stop often at attractions like the Vermont Country Store in Weston, where the famed retailer's catalog of local wares and old-school products comes to life; photogenic Moss Glen Falls; and the Ben & Jerry's Factory and Cold Hollow Cider Mill in Waterbury. Most road trippers end their trek in Stowe, but you can continue on VT-100 all the way to Newport, not far from the Canada border. The road is only two lanes its entire 216 miles, so plan for traffic on peak fall foliage weekends and again when this becomes the "Skiers' Highway" in the winter months.

The Covered Bridges of Bennington County

Vermont has the densest concentration of covered bridges of any U.S. state, and with more than 100 scattered statewide, these picturesque structures could provide inspiration for many a road trip. When your time is limited and you want to collect photos of some of Vermont's prettiest covered bridges, your best bet is this scenic drive through Bennington County in the southwestern part of the state.

Before you set out, check out Bennington's top attractions, including the Bennington Museum , with its eclectic Vermont-made artifacts and Grandma Moses paintings; the gravesite of beloved New England poet Robert Frost; and the Bennington Monument , which features an observation deck with phenomenal views. Pick up sandwiches at the Elm Street Market and head north on a route that takes in five classic, red-painted "kissing" bridges. You'll wind up at one of the oldest original covered bridges in Vermont: the 1852 West Arlington Bridge. It should come as no surprise that artist Norman Rockwell once lived steps from this picture-perfect landmark.

Jericho to Stowe Through Smugglers' Notch

Fall is an awe-inspiring time for a drive through Vermont's best-known mountain pass: Smugglers' Notch. Start your trip at the Old Red Mill in Jericho. As its name implies, this mid-19th-century mill has been a fixture on Browns River for generations. It now serves as home to the Jericho Historical Society and its museum of photos by Wilson "Snowflake" Bentley: the Vermonter who captured the first-ever images of individual snowflakes.

Start by driving east on VT-15 toward Underhill, with Vermont's highest peak, Mount Mansfield, in view. VT-15 angles north to Cambridge, then parallels the Lamoille River en route to Jeffersonville; here, you'll turn south on VT-108 for a spellbinding run through Smugglers' Notch. Twice in history, during the early 1800s and again during the Prohibition years from 1920 to 1933, this narrow passageway served as a smuggling route for illegal goods from Canada.

This is eyes-on-the-road driving and a true thrill. As you're planning your road trip, it's important to know that VT-108 is closed from mid-October through mid-May. If this is the case, continue on VT-15 until you reach VT-100; this historic route will take you the rest of the way to Stowe, one of Vermont's most iconic villages.

White River Junction to Reading: A Photographer's Dream Drive

If the goal of your road trip is to capture photos of scenes that practically scream "Vermont," pick up US-4 West in White River Junction. Soon, you'll be driving right over Quechee Gorge , known as Vermont's Little Grand Canyon; park and walk out over the gorge, or hike along the Ottauquechee River's banks. Afterwards, visit the raptors at VINS , shop and dine at the Mill at Simon Pearce , and stop to photograph the Taftsville Covered Bridge en route to the architecturally rich town of Woodstock.

You could easily spend the rest of the day in Woodstock snapping pictures of Middle Covered Bridge and the classic town green, the Jersey cows at Billings Farm and Museum , the gardens and grounds of Marsh-Billings-Rockefeller National Historical Park , and even aerial views of town if you hike up Mount Tom. But how can you resist visiting Jenne Farm ? New England's most-photographed farm is just south of Woodstock in Reading off VT-106. Continue south on VT-106, then travel west on VT-131 through protected woodlands, and pick up VT-100 North in Ludlow back to US-4.

The Vermont Cheese Trail

Where there are cows, there's cheese! And Vermont is known not only for large, world-class producers like Cabot but also for small artisan cheesemakers. Plan a delicious road trip with the Vermont Cheese Council's handy, printable Vermont Cheese Trail map , which pinpoints the locations of cheese farms and factories that are open to the public. For the ultimate cheese trip experience, start at America's oldest cheese factory, Crowley Cheese in Mount Holly; then, make stops at Plymouth Artisan Cheese in Plymouth, Vermont Farmstead Cheese Company in Windsor, and the Cabot sampling station at Quechee General Store . Be sure to bring a cooler for all of the cheeses you'll want to bring home.

Molly Stark Byway

The perfect road trip for hikers and history lovers, the Molly Stark Byway—named for the wife of the Revolutionary War "Hero of Bennington" General John Stark—is an east-west route across the southern part of Vermont. Whether you start on the western end in Bennington or the eastern end in Brattleboro, you'll follow scenic VT-9 through a region that was once the haunt of war hero Ethan Allen, poet Robert Frost, and late-bloomer artist Grandma Moses. Along the way, you'll encounter cute villages and motor right through the Green Mountain National Forest. Don't miss the view from the deck at Hogback Mountain Country Store in Marlboro. You'll find many places to park and hike, such as Molly Stark State Park, where a trail up Mt. Olga leads to a fire tower with spectacular views.

A Vermont Island Drive

Drive US-2 West out of Burlington , Vermont's largest city, and embark on an island adventure. Route 2 travels over the islands in Lake Champlain and the bridges that connect them, and is particularly enjoyable in the summer. Sample wines at Snow Farm Vineyard on South Hero Island (also known as Grand Isle) and dine lakeside at North Hero House on North Hero Island. On Isle Lamotte, Fisk Quarry Preserve and Goodsell Ridge Preserve are fascinating places to hike and to see the oldest known coral fossils. When you reach the town of Alburgh—located on a peninsula that juts down from Canada into Lake Champlain—head for Alburgh Dunes State Park and take a dip in the refreshing waters of what has often been called the sixth Great Lake.

The Northeast Kingdom

Wild and remote, Vermont's Northeast Kingdom is a gorgeous place to drive up mountains and along lake shores. Start your journey at Dog Mountain in St. Johnsbury, where you are free to roam and to appreciate the artful legacy of Stephen Huneck. From here, pick up US-2 East to VT-114 North. Watch for a right turn onto the toll road that leads to the summit of Burke Mountain, where you'll find a fire tower to climb: the views will wow you. Descend and retrace VT-114 south to Lyndon, where you'll connect to US-5 North. When US-5 turns left, continue onto VT-5A and trace the shore of Lake Willoughby, flanked by Mounts Pisgah and Hor. The beauty of this crystal-clear pool will mesmerize you; there are beaches at both the southern and northern edges of the lake.

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Take a Stunning Route 100 Vermont Fall Foliage Road Trip

By Author Tara Schatz

Posted on Published: June 25, 2023

Ready to embark on a fall foliage Vermont road trip you won’t soon forget? Route 100 in Vermont is the most scenic road in the state, especially in the fall when the trees light up the state with intense color that you have to see to believe!

At 216.6 miles, Route 100 is Vermont’s longest state highway, and is also one of the most scenic and well-loved, meandering through the Green Mountains, as well as charming New England villages.

If you love the outdoors, this Route 100 Vermont Fall Foliage road trip is a perfect getaway! There are so many great trails, not to mention waterfalls and scenic views along the way. Throw in fabulous shopping, dining, and lodging, and you’ve got all the ingredients for a spectacular fall foliage road trip.

If you’ve got five days to spend in the Green Mountains, then we have the perfect itinerary for you on Route 100. Explore all that this beautiful mountain road has to offer, from pristine lakes and waterfalls to magnificent vistas and quiet campgrounds.

The Green Mountains are a little slice of heaven for outdoor lovers of every persuasion, even when they aren’t green!

Our itinerary covers all of our favorite Vermont things: gorgeous mountain scenery, funky shops, local beers, a touch of history, and a whole lotta nature. Let’s get started!

Table of Contents

5-Day Itinerary for a Route 100 Vermont Fall Foliage Road Trip

We’ll start our Route 100 Vermont fall foliage journey in Southern Vermont, in the little town of Wilmington, and head north on Vermont Route 100 to Newport, just south of the Canadian border. This is a five-day road trip, but you can certainly complete it in fewer days, or stretch it for a week or longer.

We recommend doing this road trip in the first or second week of October. If you plan on camping, you should know that many Vermont State Park campgrounds close after Indigenous People’s Day (the second Monday in October).

Psst… Want a one-page version of this Route 100 itinerary? Sign up for our Vermont newsletter and we’ll send you a copy that you can download and/or print!

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Day 1: Wilmington, Vermont

Today you’re exploring the beautiful village of Wilmington. Relax by the lake, spend some time downtown, and eat at one of our favorite Vermont restaurants. Driving time: Depends on where you’re coming from.

It’s no secret that Wilmington is one of my favorite Vermont towns, perhaps because the lakes and mountains are so accessible here. Just south of the village is the beautiful Lake Whitingham, also known as Harriman Reservoir. Covering more than 2,000 acres, Lake Whitingham is the largest lake in Southern Vermont.

The picnic areas that surround the lake are free to use, and there are lots of great vantage points for capturing the beautiful fall colors reflected in the water. Head to Lake Whitingham early in the morning so you can capture the water when it is calm.

After you spend some time at the lake, head back into downtown Wilmington for a little meandering. The town itself is small, with only 2,000 full-time residents. You’ll find a lovely, walkable Main Street, cute stores, and plenty of restaurants. We love browsing in Bartleby’s Books, the 1836 Country Store, and Red Fox Shop.

Where to Eat: Locals love Dot’s Diner for a big, traditional breakfast, and we’d recommend Alpenglow or Folly for upscale dining.

Where to stay: If you’re looking to pitch your tent, head a few miles east to Molly Stark State Park , where you’ll find a quiet, wooded campground with private sites and hot showers. After setting up camp or before heading out in the morning, be sure to hike to the top of Mt. Olga (a 1.5-mile loop) for stunning views of the surrounding mountains – sunrise from the fire tower is the best!

If roughing it isn’t your thing, we recommend checking into the Wilmington Inn , which is located right on Main Street and very close to the Valley Trail if you want a short hike before setting out in the morning. A stay in this historic inn includes a full Vermont breakfast.

Read Next: The Best Things to Do in Wilmington, Vermont

Day 2: Wilmington to Ludlow

This section of Route 100 heads through the southern section of the Green Mountain National Forest. You’ll be stopping in several small towns, hiking along the West River, and taking in the views from the top of Mount Snow. Driving distance: 53 miles

Mount Snow: Four Seasons of Recreation Opportunities

As you head out of Wilmington on Route 100, you’ll quickly enter the town of West Dover, home of Mount Snow . This is a very popular ski mountain, but it’s open in all four seasons.

In the fall, you can enjoy lift-serviced mountain biking , or simply ride the gondola to the top of the mountain for fantastic views of the Somerset Reservoir and the surrounding Green Mountains. This is a great spot to take in fall foliage views from the top of a mountain without having to break a sweat.

The Bluebird Express gondola runs from 10 am to 5 pm between mid-June and mid-October. Lift tickets are $30 for adults (13+) and $24 for kids (5-12). Kids under 5 ride for free.

Jamaica State Park

Continue north on Route 100 until you enter the tiny town of East Jamaica, where you will turn left to stay on Route 100 (also Route 30) and head toward the village of Jamaica. While there isn’t much to the town, Jamaica State Park is a gem of a spot in both summer and fall.

The park features a rail trail, camping, and a playground. In the fall, we recommend meandering along the West River Rail trail, either on foot or on a bike if you have one with you. If you have time, hike to Hamilton Falls, a beautiful 125-foot waterfall that is beautiful in the fall, even when the water is low.

The trail to Hamilton Falls is about six miles round-trip. You can ride a bike along the river for four of those miles.

By now your tummy must be growling. For awesome burgers, sandwiches, and milkshakes, head to Honeypie on Route 30 in Jamaica. This is a quick diner-type stop, but so good!

Read Next: The Best Things to Do in Jamaica State Park

Weston, VT : Visit the Vermont Country Store

Weston is another one of those picturesque New England villages, complete with a little town green, several unique stores, and the famous Weston Playhouse. Shopping in Weston is like taking a step back in time, so that’s what’s on the agenda.

Located across from the village green on Main Street, the Vermont Country Store is a step back in time you won’t want to miss. The aisles are stocked to the rafters with penny candy, maple syrup, apothecary items, household goods, and lots of local goodies.

Browse the crowded aisles to discover the largest collection of weathervanes in Vermont, the Vermont Scale Museum, and a year-round Christmas shop. And speaking of Christmas, no matter what time of year you visit the Vermont Country Store, it’s always a good time to grab some one-of-a-kind Vermont gifts for your friends and family back home.

Explore the Village of Ludlow, Vermont

Finally, make your way to Ludlow, Vermont, located in Okemo Valley and home to Okemo Mountain Resort. Ludlow is a small community, but you will find a few unique shopping and dining opportunities, as well as several trails. Be sure to visit Buttermilk Falls while here. This lovely waterfall is a popular swimming hole in the summer, and stunning in the fall.

Where to eat and sleep: For really unique dining, check out Homestyle Hotel and then head over to their sister property, Main + Mountain across the street to spend the night. Homestyle Hotel is a small neighborhood restaurant serving local fare, and Main + Mountain features beautiful, eclectic lodging.

For dining at the Homestyle Hotel restaurant, we recommend making reservations well in advance. This is a busy area during fall foliage season, and it’s a small space!

Day 3: Ludlow to Waitsfield

This section of route 100 is characterized by very small towns, mountainous terrain, and acres of farmland. For much of the drive, you will follow the eastern slope of the Green Mountains, along the border of the Green Mountain National Forest. There are too many fun stops to mention, so I’m going to focus on my favorites. Driving distance: 70 miles

Plymouth Notch, VT : Visit the Calvin Coolidge State Historic Site

About 18 miles north of Ludlow, turn right on Route 100A and drive a mile to President Calvin Coolidge State Historic Site . Plymouth Notch is the birthplace and boyhood home of our 30th president, and his homestead and the surrounding village are virtually unchanged since the 20th century.

The village is known as the Plymouth Notch Historic District and is on the National Register of Historic Places. Meander around the 600 acres, visit the Calvin Coolidge Museum and Education Center and check out dozens of historically preserved buildings.

Long Trail Brewing Company

After leaving Plymouth, continue north on 100A to the town of Bridgewater Corners, where you’ll find the famous Long Trail Brewing Company . This quaint riverside pub and restaurant is the perfect lunch spot, and the view is pretty great too! In addition to their popular Long Trail Ale, they make a variety of delicious seasonal craft beers.

Moss Glen Falls, Granville , VT

Moss Glen Falls in Granville makes our list of the most beautiful waterfalls in Vermont . This picturesque waterfall is more of a roadside attraction than anything else, but it’s definitely worth a visit. Because Moss Glen Falls is located right off of Vermont Route 100, it will only take a few minutes to check it out. Bring your camera!

Follow the short boardwalk into the woods and check out the falls from the viewing platform. Because this is such an easy waterfall to see from the road, expect to share the spot with dozens of other leaf peepers.

From here, you’ll be heading into the beautiful Mad River Valley. If you have time, drive some of the back roads in the area, which are rural and full of character.

Dining and Lodging in Waitsfield, VT

Where to stay: After a long day of driving, exploring, and taking photos, it’s time to settle in for the night. The village of Waitsfield is a great little town with a few unique places to stay and eat. For a bit of luxury to go with your leaf-peeping, we recommend the The Griff Inn , which is a beautiful solar-powered inn with seven guest rooms and luxuriously comfortable beds.

If you are looking to spend less on your accommodations, check out Mad River Lodge , which provides standard rooms and suites and contactless check-in. While the rooms are basic, they are very clean and the location is great for exploring all of the Mad River Valley.

Where to eat: American Flatbread Pizza — undoubtedly the best wood-fired pizza in the state of Vermont.

Day 4: Waitsfield to Stowe

You won’t be driving much today because this section of Vermont Route 100 is packed with things to do! The Waterbury/Stowe area is a beautiful (and popular) fall foliage destination, and if you’re feeling short on time, I urge you to give it an extra day. Here are some of our favorite tourist attractions and natural areas on route 100 between Waitsfield and Stowe. Driving distance: 24 miles

Waterbury, VT : Home of Ben & Jerry’s Ice Cream

Waterbury is about 14 miles north of Waitsfield, so you can dive right into your fall foliage adventures without having to drive much. It’s home to Ben & Jerry’s Factory Store, where guided tours are offered daily. Learn how Vermont’s famous ice cream is made, and be sure to stop at the flavor graveyard to pay your respects to the “dearly de-pinted”.

After your tour and tasting, head to Waterbury Center State Park , which is located just off of Route 100 and is one of our favorite spots for paddling, fishing, picnicking, and remote camping. If you visit in the fall, you can hike a short trail along the lake for great fall foliage views.

There is front-country camping available on Waterbury Reservoir at Little River State Park , which is our top state park for kids in the whole state. This park is open until October 23rd, and there are camping cabins that you can rent if staying warm and sleeping in a bed is crucial. If you don’t want to camp, we recommend staying a few miles north in Stowe.

Just a half-mile from Waterbury Center State Park is Cold Hollow Cider Mill . Not only is this one of Vermont’s top tourist attractions, but they also have pretty delicious cider donuts. Pop in for lunch or some fresh baked goods, and don’t forget a gallon of cider for your cooler!

Fall in Stowe, VT : Home to Vermont’s Highest Peak

Stowe is known as a ski town, but it’s equally lovely in the summer and fall, with all kinds of shops, restaurants, and coffee shops to explore.

At 4,395 feet, Mt. Mansfield in Stowe is Vermont’s highest mountain. On a clear day, you can see west to Lake Champlain, north to Canada, and east to New Hampshire. There are several trails leading to the top, but if you don’t have time for an all-day hike, consider driving the auto-toll road or riding the gondola to the top of the mountain from Stowe Mountain Resort.

The toll road takes you right to the top of Mt. Mansfield, the peak that is locally called “the Nose.” From the Nose, you can hike along the ridge of the mountain to the Chin (2.8 miles round trip), which is the official highest point in Vermont.

The top of Mt. Mansfield is one of two areas in the state where you can find an alpine tundra ecosystem. This is a very fragile area, and hikers are asked to stay on marked trails and to keep dogs leashed at all times.

After your hike, be sure to stop at The Alchemist  to try out New England’s most famous beer, Heady Topper. This iconic brewery is located on Cottage Club Road in the village of Stowe. You will likely meet many fellow road trippers here — people come from near and far to stock up on the Alchemist brews. You are usually limited to 6 four packs of any variety.

If you have time, take a side trip through Smuggler’s Notch on Route 108. This is a narrow pass through Mt. Mansfield and Spruce Peak, but not suitable for RVs. The roadside is flocked by huge boulders and dark caves, perfect for scrambling around.

There are several trails along the roadside, including a lovely hike to Bingham Falls. The trail is an easy 1.6 miles round trip and brings you to one of the state’s most lovely waterfalls.

Where to Stay: There are numerous lodging options in Stowe, and we would be hard-pressed to pick a favorite. The iconic Trapp Family Lodge is a gorgeous mountain retreat with miles of hiking trails, an onsite brewery and restaurant, and indoor/outdoor pools.

Where to Eat: Doc Ponds has a limited menu, but those tacos are divine! Have a root beer float for dessert and you’ll be golden ’till morning.

Read Next: The Best Hikes in Stowe, Vermont

Day 5: Stowe to Newport

The last leg of your road trip on Vermont Route 100 is characterized by a wild stretch of road. The further north you go, the better your chances of seeing one of North America’s largest mammals, the massive moose. Be on the lookout for these gentle giants, especially along the roadside, where they pose a threat to unsuspecting motorists. Driving Distance: 48 miles

Newport, VT : Where Vermont Meets Canada

As you head out of Stowe and into Hyde Park, be sure to take in the spectacular views of Mt. Mansfield behind you. You have entered the famous Northeast Kingdom, an area known for its wild and rugged beauty . Heading north, you’ll pass through several small towns, including Eden, Lowell, Westfield, and Troy, before heading into the relative metropolis of Newport.

Located on the shores of Lake Memphremagog, Newport is a bustling place these days. Main Street is lined with restaurants, boutiques, and galleries. Several waterfront overlooks allow you to take in the majestic views of the massive glacial lake, which covers 41 square miles.

The Newport Bebee Bike Path starts in the downtown area and runs for about six miles along the shore of the lake and into Canada (bring your passport if you choose to cross the border). Rent bikes (or kayaks) at The Great Outdoors to start exploring!

For another fun excursion, head to the Haskell Free Library & Opera House , where you can stand in both Vermont and Quebec at the same time. If you are lucky enough to visit the opera house for a show, you can sit in Vermont and watch the performers on stage in Canada!

Where to Eat: Try the Derby Line Village Inn for spectacular German cuisine, or Eastside Restaurant & Pub for traditional American Fare. If you’re looking for the best Thai and sushi in the Northeast Kingdom, you have to try Dusit Thai Cuisine . The owners relocated from Thailand in 2015, and have been wowing locals and visitors with their delicacies ever since.

Where to Stay: Your first impression of Newport City Inn may be that it’s a run-down roadside motel, but beneath the surface, it’s a gem! The rooms are beautifully decorated and spacious and there’s a great indoor pool too.

Need more room to spread out? This beautiful lakefront cottage sleeps four comfortably in a peaceful setting on South Bay.

Where to Camp: With 75 huge campsites for both tents and RVs, a swimming beach, and a playground area, Prouty Beach & Campground is a fun and inexpensive way to explore Newport and the surrounding communities. It’s a county park, right next to the bike path, and less than a mile from downtown Newport.

Read Next: Take a 5-Day Road Trip on Route 7 in Vermont

Where to Next?

After completing your route 100 Vermont fall foliage road trip through the mountains from south to north, you can easily hop on Interstate 91 in Newport, which will whisk you away to points south.

If you’re up for further adventures, you can head north into Canada (Montreal is two hours away), southwest into Burlington and the Champlain Valley, or south on the Connecticut River Byway.

Vermont Route 100 Fall Road Trip FAQs

We get a lot of questions about traveling through Vermont, so we just wanted to take some time to answer the ones we get most often. If you have any other questions about road tripping through Vermont, simply leave a comment and we’ll answer ASAP.

Should we drive Route 100 in Vermont from south to north or north to south?

We recommend driving this route from south to north. Why? Because the southern end of route 100 is closer to major metropolitan areas and airports. The beginning of this road trip is 60 miles from Albany International Airport in New York, 126 miles from Logan International Airport in Boston, and 205 miles from JFK in New York City.

Once you’ve completed the 189-mile drive on Route 100 from Wilmington to Newport, you can hop onto Interstate 91 and head south again.

When is the best time to see fall foliage on Route 100 in Vermont?

You will see fall colors on Route 100 from late September through most of October. October is the busiest month for tourists in Vermont, who come from all over to see the leaves change.

The speed limit on Route 100 varies wildly from 25 mph in town centers to 50 mph between towns, so no matter what time of year you plan to drive it, plan on taking your time!

Will we have access to amenities on Route 100?

Yes! One of the most beautiful things about a Vermont Route 100 road trip is that you travel through the Green Mountain National Forest and the mountains, but you’re never very far from a village or town, which means you’ll have easy access to gas stations, grocery stores, hotels, and campgrounds.

What to Pack for Your Vermont Route 100 Road Trip

Not sure what to pack for your Route 100 Vermont fall foliage road trip? Keep it casual! You’ll be doing a lot of outdoor adventuring, and even the in-town activities (shopping, museums, and restaurants) don’t require fancy duds.

One thing you won’t find much of on Route 100 is nightlife, so leave the fancy dress and high heels behind. Here are some more packing must-haves to help you make the most of your trip.

• Activewear – Nothing heavy-duty, but you’ll be spending some time outdoors and you want to be comfy. Opt for sturdy non-cotton pants ( like these ) and a breathable, moisture-wicking shirt. I love Merino wool shirts because they keep you cool when it’s hot out and warm when it’s cold out, plus they don’t stink like polyester blends and they dry quickly.
• Sturdy shoes – Again, you want your feet to take you wherever you need to go. Rugged trail shoes or waterproof hiking boots would be my suggestion.
• Jackets – The weather in Vermont is fickle, especially in the mountains. For fall travel, pack a down puffy jacket and a wool hat. These down jackets pack down really small and are perfect for travel.
• Camera – Perhaps your phone doubles as your camera. Awesome! If your phone camera doesn’t take great photos, consider bringing a separate camera to capture all the beautiful scenery. If you want a dedicated point-and-shoot camera that packs neatly into a backpack, check out the Canon PowerShot SX620 . Overall, this little camera takes better photos than the best smartphone with a powerful zoom and 4K video. I love traveling with mine, and it’s great for saving your phone’s battery!

Resources for Planning Your Vermont Road Trip Itinerary on Route 100

We’ve been traveling around Vermont for a pretty long time, but we’re always discovering new places to go and cool things to see. Here are the books, maps, and resources we used to plan this journey.

• For great book recommendations about adventuring in Vermont, read:   Books About Vermont for Exploring Like a Local .
• Vermont Department of Tourism and Marketing – This is our one-stop shop for finding cool things to do throughout the state. Sign up for their mailing list or order a free vacation guide before your trip.
• Discover Newport Vermont – Plan your stay in Newport and the surrounding communities.
• Go Stowe – All the happenings in and around Stowe, VT

What’s your favorite fall foliage road trip in Vermont? Share it with our readers in the comments below.

Get this complete itinerary in a one-page printable version!

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Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers , an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.

Bruce Cripps

Tuesday 30th of January 2024

Live in UK - planning New England vacation in October - driving Boston > Cape Cod > Kennebunkport > Jackson NH > Woodstock via Route 100 > Stockbridge via Route 100 > Boston.

Booked to stay in Woodstock for 2 nights and would like to identify best scenic drives around Woodstock. Have tried and failed to make contact with Woodstock Visitor Centre. Can you please make recommendations or direct me to the best source/s.

Many thanks.

Tara Schatz

Hi Bruce, There are lots of gorgeous back roads just south and north of Woodstock, and while cell service is spotty in much of Vermont, my GPS has never let me down around Woodstock. Go to Sugarbush Farm to taste cheese and maple syrup, drive through the Village of Pomfret, and visit the covered bridges. Here's a link to a map of the covered bridges in the area. https://www.google.com/maps/d/viewer?mid=1rccS98vMbkFrUPbGEvCscRfssRRo5Ps&usp=sharing

Sunday 1st of October 2023

Indigenous peoples day? Do you mean Columbus’ day? Gimme a woke break…

Saturday 7th of October 2023

@Norbert, By "woke" do you mean educated? Columbus didn't discover America. People were already here; people he brought disease, violence and slavery to. Take the time to inform yourself, including about Columbus and the Taino.

Wednesday 4th of October 2023

Like it or not, Indigenous Peoples' Day is the official state holiday in Vermont. Take up your issue with the state...

Robert Vinck

Sunday 22nd of May 2022

Hi, what airport is the closet when we are done with the Itinary?

Hi Robert -

If you are heading north from Wilmington to Newport, Burlington International Airport (BTV) is about two hours away. A night in Burlington would make a great last day/night of the itinerary too.

Friday 11th of March 2022

Very useful information thx!

45 Places to Stop on Your Ultimate Vermont Road Trip

We’ve used our experience and research for road tripping in Vermont to put together the Ultimate Vermont Road Trip Guide. Use these suggestions to plan your trip and you’re sure to have an amazing time!

Table of Contents

Northern Vermont

Our Vermont road trip plan starts in the northern part of the state. In our opinion, this is the best place to go for outdoor fun. Not only are there plenty of hiking trails, mountain biking trails, and waterfalls in the area, you’ll also find the beautiful Lake Champlain in northern Vermont, meaning water recreation is an option. Of course, the ski resorts are also fantastic if you find yourself visiting during the winter months. 

Not into the outdoors? Not to worry, there are also plenty of museums, tours, delicious cider mills, maple farms, and more in northern Vermont. You’re sure to find plenty to do while you’re there. 

Here we are kicking off our east coast road trip with our first stop in Vermont:

Stowe Vermont

Start your Vermont road trip in Stowe,VT. Stowe is easily one of the best towns in the state to visit. It is chock-full of amazing things to see and do, and the variety really keeps things interesting. This place has been dubbed the “Ski Capital of the East,” but we find it’s a wonderful place to check out no matter the time of year. 

Some of our favorite Stowe attractions include:

Highway 108 Scenic Drive

Those who want to take in all the beauty of the Vermont countryside should really consider a drive through Smugglers Notch on Highway 108. This scenic route provides some of the prettiest views in the state, especially if you happen to be taking the scenic drive during autumn when the fall foliage creates a rainbow of colors along the way. 

Moss Glen Falls Hike

Hiking is everywhere in northern Vermont. One of the very best options is the Moss Glen Falls Hike. This is a fairly easy trail that takes you through the woods to a beautiful waterfall. If you choose to go only to the falls and back, it’s a mere 0.6-mile trek. Those who do the entire trail will be looking at about 4.2 miles of hiking. 

We also really liked hiking to Bingham Falls. It’s great if you prefer a super easy hike with a nice reward at the end. 

Mount Mansfield Auto Toll Road

The highest peak in Vermont, Mount Mansfield offers awesome views of the surrounding area. Luckily, taking in these views does not require a strenuous hike. Instead, you can drive to the top via the auto toll road. Just be prepared for a steep and winding drive that is not for the faint of heart. 

Cabot Cheese Store

Ever had some Vermont cheese? If not, a visit to the Cabot Cheese Store is a must. This store is just a short drive from Stowe, so be sure to plan a visit during your stint in the town. It’s a big store with plenty of variety, and samples are available to help you decide what to buy. 

Emilys Covered Bridge

Covered bridges are everywhere in Vermont, and we recommend going on a covered bridge tour when you make it down to Bennington. That said, Emily’s Covered Bridge in the Stowe area is pretty enough, and it has a cool enough story that we do recommend making a special trip just to see it and play in the water that runs under it. Just make sure you read the story behind the bridge first!

Check out our time in Stowe, Vermont:

Stowe Mountain Resort

If you’re taking a Vermont road trip in the winter months, skiing is a must-do. One of the best places to do this? Stowe Mountain Resort . Here, you’ll find skiing opportunities for people of all ages and levels, as well as snowboarding, hiking, biking, and plenty of delicious restaurants. 

Ben & Jerrys Factory Tour

Did you know Vermont is home to the famous Ben & Jerry’s Ice Cream we all love? Not only that, guests are even invited to tour the factory to see how the stuff is made! Other fun things to do at this attraction include checking out the “flavor graveyard” and grabbing a treat from the onsite Scoop Shop. 

Vermont Ski and Snowboard Museum

Skiing and snowboarding are important parts of Vermont culture. Yes, you should definitely try these sports for yourself if you are visiting during the snowy months. That said, you can also learn about skiing and snowboarding by visiting the Vermont Ski and Snowboard Museum. 

Smugglers Notch State Park

Named for a narrow pass through the Green Mountains, Smugglers Notch State Park is a beautiful park. It features incredible cliffs, gorgeous vistas, a picnic area by a stream, and wonderful hiking trails. Other fun things to do in the park include bouldering, ice climbing, cave exploring, and biking. 

Cold Hollow Cider Mill

Most people are aware that Vermont is known for its cider. Why not watch some fresh Vermont cider being made? At Cold Hollow Cider Mill, you can do just that while sipping on a cup of the stuff. After you’ve finished your cider, be sure to pick up some fresh cider donuts and some more cider to take home!

Where to Eat

The backyard.

An amazing dinner experience can be found at The Backyard. The outdoor seating here is lovely, and the restaurant has an excellent selection of food and drinks. We recommend sitting near the outdoor firepit if at all possible. 

Stowe Cider

Cold Hollow Cider is great, but if you’re looking for even more fantastic cider, head to Stowe Cider. Here, you can sit (both indoor and outdoor seating are available) and sample a variety of ciders. You might also get lucky and be at the cidery when a local food truck is parked outside.

The Alchemist

Touted as “the best brewery in the U.S.,” The Alchemist is a must-try spot for beer fanatics. Our favorite option here? The Heady Topper beer. That said, any brew you try is likely to be wonderful. 

More Information on Stowe

20 Fun Things To Do in Stowe, Vermont

If you only have a weekend be sure to check out this great post on a Vermont weekend getaway !

Burlington Vermont

Another beautiful city, Burlington should be on every Vermont road trip list. This place is located right on Lake Champlain, so expect beautiful views and beaches. You’ll also find great places to bike and some awesome spots to learn something new. 

Some of the very best things to do in Burlington are: 

Church Street Marketplace

An awesome shopping district located in downtown Burlington, Church Street Marketplace is an excellent place to do some souvenir shopping. The district covers a full four blocks and plays host to numerous local shops and eateries, as well as street performers that set up shop on nearly every corner. 

Lake Champlain Waterfront

Lake Chaplain is seriously gorgeous and well worth visiting several times during your Vermont road trip. We especially love heading to the Lake Champlain waterfront in Burlington to stroll along the boardwalk and watch the sun go down over the water. 

Green Mountain Railroad

Looking for yet another way to enjoy the beauty of the Vermont countryside? Hop on a Green Mountain Railroad train. This awesome tour company offers a variety of different types of rides through some of the prettiest parts of the state, allowing you to see this beauty from a different point of view. 

Ethan Allen Homestead Museum

Most people have heard of Ethan Allen, but many don’t realize that the man played such an important role in protecting Vermont homesteading rights. Additionally, he aided the Continental Army during the Revolutionary War. Visit his homestead to learn all about this incredible man. 

ECHO Leahy Center

Lake Champlain is a prominent feature of northern Vermont. What many don’t realize is the role the lake serves in the environment. Visit the ECHO Leahy Center to learn about the ecosystems in the lake and how they work together to create the beautiful northern Vermont environment we love. 

Citizen Cider

Yet another fantastic place for cider, Citizen Cider is the perfect dinner spot. Get a flight of cider to try some interesting flavors, and be sure to try the poutine, which the restaurant is well known for. 

Foam Brewery

For lovely outdoor seating, great craft beers, and even more cider options, head to Foam Brewery. This is a favorite of locals and visitors alike, and once you visit, you’ll understand why. 

Creemees Ice Cream

Finally, you’ll want to round out at least one day with ice cream from Creemees. This place is located on the Lake Champlain waterfront, meaning you can grab a scoop (we recommend the maple flavor) and watch the gorgeous sunset. 

More Information on Burlington

15 Fun Things to do in Burlington, VT

Shelburne Vermont

Located just a little bit south of Burlington, Shelburne has a surprising number of excellent attractions to offer. Therefore, we felt it had to be included in our Vermont road trip itinerary. That said, you could easily visit Shelburne while staying in Burlington if you prefer to change lodging less often. 

Our favorite Shelburne attractions are listed below.

Shelburne Museum

Several historic buildings stand on the gorgeous campus of Shelburne Museum . Each of these lovely buildings is home to exhibits on art, history, nature, and more. The exhibits are so varied that there is sure to be something for everyone, and if you ask us, the grounds and buildings are just as interesting as the exhibits. 

Vermont Teddy Bear Factory

In addition to producing delicious ice cream, Vermont also puts out some seriously adorable teddy bears. These are made by the Vermont Teddy Bear Factory in Shelburne, where guests are invited to tour the facility and see just how these stuffed friends are put together. You can also create your own bear or send a favorite teddy to the “doctor” to get fixed up. 

Lake Champlain Chocolates

Syrup and cider are two foods Vermont is known for, but did you know that the state also puts out some seriously good chocolates? Some of the best are from Lake Champlain Chocolates. Their candies are made from locally sourced ingredients, and they offer a free 30-minute tour (complete with a tasting!) to anyone who stops in. 

Shelburne Farms

An enormous working farm, Shelburne Farms is an excellent place to learn all about Vermont farm life. This attraction is home to a non-profit that works to educate visitors on how to create a sustainable future. Environmental educational programs happen on a regular basis at the farm, and walking trails, a historical barn filled with animals, and an onsite restaurant all help to make it an exciting experience.

Where to Stay

Courtyard burlington harbor.

Our favorite hotel in the northern Vermont area, Courtyard Burlington Harbor features all kinds of amazing amenities. The saltwater pool is perfect for relaxing after a long day of adventuring, and the onsite restaurant makes meals easy. Guests also love sitting around the outdoor firepit to unwind.

Serene Country Cabin

The perfect escape into the Vermont countryside, the Serene Country Cabin is a great pick for your time in Stowe. The cabin is just a few minutes away from the town, and is also near skiing and other outdoor recreation opportunities. It includes amenities such as an outdoor fire pit, cable TV, and books and games.

White Caps Campground

Prefer to camp during your time in northern Vermont? White Caps Campground is a great pick. This beautiful place is located at the south end of Lake Willoughby and has spots for tents and RVs, as well as some rental cabins. Onsite activities include hiking, paddling, and swimming.

Central Vermont

After you’ve spent a week or two in the northern part of the state, you’ll want to continue your Vermont road trip and head on down to central Vermont. This area is home to the state capitol. It’s also a fantastic place to learn a bit of history.

Of course, you’ll find some outdoorsy fun here too, including an absolutely stunning state park that is a Vermont must-see. Other fun sights include art galleries, adorable local boutiques, and yummy local restaurants.

Montpelier Vermont

It might be the smallest capital city in the country, but Montpelier isn’t lacking when it comes to character or things to do. Local boutiques and restaurants are around every corner, the historic downtown area and pretty park provide great places for a stroll, the nightlife scene is surprisingly fun, and galleries, theaters, and music venues all work together to keep the arts alive. 

Want to find the best attractions in Montpelier? We’ve got you covered below:

Rock of Ages

Start your tour of Rock of Ages in the beautiful modern visitor center where you can watch a video about quarrying, shop for stone souvenirs, and of course, book your quarry tour ticket. When it’s time for your tour, you will be taken to see the largest operating deep-hole dimension granite quarry in the world. This is an astounding sight to see, and a unique experience for sure. 

Morse Farm Maple Sugarworks 

Maple syrup is one food item that just screams Vermont. For this reason, we highly recommend touring at least one maple farm while in the state. Morse Farm Maple Sugarworks is a great choice. Here, you can tour the grounds either on foot or via motorcoach. There are also videos that provide plenty of information and even a free treat at the end of the tour. 

Looking for another great maple farm option? We also loved Sugartree Maple Farm. 

Sarducci’s Italian Food

For great Italian food, you simply must go to Sarducci’s while in Montpelier. This is easily one of the best restaurants in the city, and has options for picky eaters and adventurous palates alike. Best of all, the outdoor seating overlooks the river, meaning you’ll have a great dinner and a great view. 

Woodstock Vermont

A small and picturesque place off of Route 100, Woodstock may be quiet and laid-back, but that certainly doesn’t mean it’s a boring place. In fact, the town might just be one of the best tourist destinations in the state. Biking, golfing, and fishing are popular activities in the town, and the dozens of bed-and-breakfasts ensure everyone has a place to lay their head after a day of exploring.

Not sure what to do when you get to Woodstock? Here are our favorite options:

Quechee Gorge State Park

Home to some of the most unique landscapes in Vermont, Quechee Gorge State Park is the perfect place to go for a long hike and some fantastic photo opportunities. The gorge is the deepest in Vermont, and is often referred to as “Vermont’s Grand Canyon.” That said, the green scenery is nothing like what you find at the Grand Canyon, yet still incredibly beautiful.

Marsh-Billings-Rockefeller National Historical Park

The Marsh-Billings-Rockefeller National Historical Park is a lovely place that is full of history and natural beauty. It was once a forest and dairy farm owned and operated by Frederick Billings, and is named for Billings and his co-owners. It’s a wonderful place to explore, and we’re betting you’ll learn something new while you’re there. 

Billings Farm and Museum

An absolutely fantastic open air museum, Billings Farm and Museum is home to a fully operational Jersey cow farm, as well as a restored historic home that serves as a museum. Learn about the history and culture of the state and then head outdoors to get hands-on and learn about animals. 

Comfort Inn and Suites at Maplewood

Need a hotel in central Vermont? We’ve got you covered. This Comfort Inn and Suites is incredibly well reviewed for a reason. The staff are on top of things, everything is clean and well-kept and the hotel is in an excellent location. 

Cottage on the Hill

Located between Montpelier and Woodstock, this Cottage on the Hill is an awesome home base for your time in central Vermont. Not only is it absolutely adorable, it’s also functional and comfortable, boasting amenities like a fireplace, a washer and dryer, and a fully equipped kitchen.

Southern Vermont

Finally, you will probably want to mosey on down to southern Vermont to round out your Vermont road trip. While this part of the state doesn’t have quite as many attractions as the northern area, the things you will find in this area are still well worth stopping for.

We love the history lessons found in south Vermont, and the museums are some of the most unique we’ve found. Of course, we can’t fail to mention the fantastic fly fishing opportunities found in the area. 

Manchester Vermont

Manchester is another quaint Vermont town. This one is tucked away in the Green Mountain National Forest, providing the perfect escape from the hustle and bustle of the bigger city. If you’re looking for a taste of rural Vermont, this is the place to go. 

The best Manchester attractions include:

Hildene: The Lincoln Family Home

First owned by President Lincoln’s son, Robert Todd Lincoln, Hildene was passed from one generation of the Lincoln family to the next for many years. In 1975, the home was purchased and restored to its original glory, and is now open to visitors who can tour the house and grounds. 

American Museum of Fly Fishing

Fly fishing is a popular pastime in the state of Vermont. Therefore, it should come as no surprise that the state is also home to an entire fly fishing museum. Wander the American Museum of Fly Fishing to learn all about fly fishing and the history behind it. 

The Vermont Country Store

If you head north of Manchester you will eventually make your way to the Vermont Country Store . This adorable general store has all the New England country charm you could ever want, and is the perfect place for browsing for souvenirs. 

Bennington Vermont

Not too much further south you’ll find the city of Bennington. This city has a lovely collection of covered bridges that absolutely must be checked out when you’re there. It’s also home to a number of excellent museums, so make sure you schedule at least a few days to explore the place. 

Below are the must-dos in Bennington:

Robert Frost Stone House Museum

Robert Frost is a well known poet. Nearly everyone has read the man’s poetry at some point, and many consider him a genius wordsmith. At the Robert Frost Stone House Museum, you can tour the home of this amazing writer and learn a bit about the life and times of the man. 

The Bennington Battle Monument

Built to commemorate The Battle of Bennington, which took place on August 16th, 1777 during the Revolutionary War, the Bennington Battle Monument is a must-see when in the area. The monument is a 306-foot-high stone obelisk. Events often take place at the monument, and there is an observation floor in the monument that provides excellent views. 

Bennington Museum

The perfect place for art fanatics, Bennington Museum focuses on art made in New York, New Hampshire, and Vermont. Here you’ll find art from the 1700s, as well as more modern pieces. One of the museum’s most notable features? Its enormous collection of Grandma Moses paintings. This is the largest collection in the world from this artist. 

Cozy Mountain Retreat

Nothing says Vermont quite like a cozy little cottage in the woods, and that is exactly what you’ll find at this Cozy Mountain Retreat . Stay here to escape into nature while still remaining close enough to local attractions. Enjoy fast internet, a nice grill, and more.

Manchester View

Get a room at the Manchester View and you will be minutes from Route 7, as it is located in Green Mountain National Forest. The rooms are all non-smoking and equipped with wi-fi. You can even splurge and upgrade to a room with a fireplace and hot tub!

Pine Hollow Campground

Want to camp in south Vermont? If so, Pine Hollow Campground is the spot for you. This lovely campground is located just a few minutes south of Bennington, meaning you won’t have to drive far to see local attractions. That said, you might just be tempted to stay within the campground most of the time, considering the gorgeous views and outdoor recreation opportunities found there.

There you have it, 45 amazing stops so you can hit the road on your Vermont road trip we hope you enjoy your time exploring the Green Mountain State!

Want even more information on visiting the incredible state of Vermont? Check out

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7 Day Vermont Road Trip Itinerary

Last updated on March 11th, 2024

Looking for a perfect Vermont road trip? We’re sharing our itinerary from our 7 days in Vermont, including hikes, local businesses, and beautiful scenery! Visiting New England, especially in the fall, had been a US bucket list item for us for years. We dreamt of exploring charming small towns, hiking in the mountains, and seeing gorgeous fall foliage, and finally this past fall we were able to make it happen!  Our fall New England road trip kicked off in Vermont and despite knowing we would really enjoy the state, we were surprised by how much we loved it! The people were so incredibly friendly, the scenery, with mountains, farms, and lakes, was gorgeous, and the towns were just as adorable as we had hoped.

Watch all of our adventures in Vermont , including learning about maple syrup, visiting different cities and towns, and going for beautiful hikes!

And in this guide we’re sharing a 7 day Vermont road trip itinerary, which is almost identical to our exact route. It will not include every single place to visit in Vermont, but rather the places we loved and highly recommend, which would be great for a first visit to the state!

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About Vermont

Vermont road trip route, when to visit vermont, where to stay during your vermont road trip, things to know before your vermont road trip, what to bring on your vermont road trip.

Vermont is located in New England in the northeastern part of the United States and is nicknamed the Green Mountain State, after the Green Mountains, which run north to south, like a spine going through the entire state. In fact, the name Vermont actually comes from a combination of two French words: “vert”, which means green, and “mont,” which means mountain. Vermont was the first state admitted to the Union after the original 13 colonies and is the 6th smallest state by area. It is also the second least populous state after Wyoming, with the largest city in the state, Burlington, only having 44,743 people and is the only state without a building taller than 124 feet.

What Vermont may lack in size and number of people, it makes up for in endless scenery, open spaces that aren’t overly developed, and four seasons worth of activities. It is even home to some major companies, like Ben & Jerry’s and Orvis, and is the largest maple syrup producer in the United States.  There is just something magical about Vermont that is hard to put into words, but even in just a week in the state, we fell madly in love with it and are already dreaming of returning.

Before embarking on your adventure, please review the  Leave No Trace principles  to ensure you leave every place better than you found it, so that others can enjoy these beautiful places for many years to come! These seven principles include planning ahead and preparing, hiking and camping on durable surfaces, disposing of waste properly (pack out what you pack in!), understanding campfire rules and always fully extinguishing your fires, respecting wildlife, and being considerate of other visitors. 

There are many things to do and places to explore in Vermont, but for this guide we’ll be focusing on the areas we personally visited during our time in Vermont, which we highly recommend for first timers to the state who want to experience some of its best sights! Here is the route that this Vermont road trip itinerary will be following.

Flying to Vermont

This route map above assumes you’ll be flying to visit Vermont and the best airport to fly into will be the Boston Logan International Airport (BOS) , which is a massive airport that is serviced by all major airlines and offers nonstop flights from many destinations in the United States. The drive from Boston to the first stop in Vermont will be about 2.5 hours, so it’s not super close, but Boston is also a great gateway to other areas in New England if you plan to explore other states while visiting Vermont.

Driving to Vermont

If you’re driving to Vermont, the road trip route above may need to be modified a bit, as your road trip will possibly start and end in different places. You also may want to do the route in reverse depending on where you’re coming from. Here is how long you can expect to be on the road if arriving from other nearby destinations: Lincoln, NH: 1 hour, 40 minutes (76 miles) Hartford, CT: 2.5 hours (147 miles) Lake Placid, NY: 3 hours (128 miles), which includes a ferry across Lake Champlain Portland, ME: 3 hours (181 miles) Providence, RI : 3 hours, 15 minutes (189 miles) New York, NY: 4.5 hours (263 miles) Note: some of the roads and times above include driving tolls. If you want to avoid paying for tolls, make sure to turn off tolls on your Google Maps settings.

How to get around Vermont

Since this is a road trip itinerary, you’ll definitely need to rent a car or drive your own to fully enjoy all of the sights on this guide, as public transportation isn’t really an option between all of the towns without hiring a tour guide. Assuming you’re visiting in the summer or fall, any type of vehicle will work just fine on a road trip around Vermont, as none of these stops require 4×4 to get to. Our Sprinter van was able to navigate Vermont well and we didn’t run into too many issues parking a larger vehicle either!

Vermont offers activities for all four seasons, including skiing in the winter, fresh maple syrup in the spring, hiking in the summer, and gorgeous foliage in the fall.  However, this guide is focused on visiting Vermont in the summer or fall , when the trails are snow free and less muddy than the spring. Here’s what you can expect when visiting during these two seasons!

Summer in Vermont 

The summers in Vermont are beautiful, with an average high temperature between 70-80 degrees fahrenheit, depending on where you visit (Burlington tends to be warmer than Stowe). With lots of state parks, forests, lakes, and outdoor activities, this is one of the best times to explore Vermont if you want to comfortably enjoy all of the beautiful scenery the state has to offer. It can be busier though, since after a long winter many locals and visitors are eager to get out and explore!

Fall in Vermont

When we think of Vermont, we think of the colorful fall foliage that the state is famous for. And we aren’t the only ones! Fall is a popular time to visit Vermont, especially during peak foliage, but we didn’t find the crowds to be too horrific during our visit. Besides the foliage, the weather during the fall is really nice, with cooler temperatures and a mix of sunny days and some foggier days. Note: Peak foliage can vary year to year and timing also varies depending on the region. When we visited in late September, we were a bit too early for Stowe, but managed to see some great colors in the Northeast Kingdom. Based on our experience visiting in fall 2021, the first week of October would be a safer bet to find some bright colors, but for real time updates, we found this website to be helpful.

Since this road trip itinerary covers quite a bit of ground, we’d suggest staying in different places throughout the trip to limit how much time you spend driving each day. We will include suggestions of places to stay under each day of the itinerary! However, if you want to stay in one place the entire time and do not mind some driving, Waterbury or Stowe will be the best spots, as they are under 2 hours (one way) from each destination, so you could do day trips to every spot on this guide. We will list some options of places to stay in Waterbury or Stowe on day 3 of this guide!

Curious how we get FREE flights and hotels? Check out our list of our favorite travel cards that have saved us thousands of dollars!

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Before you go, here are a few important things to know before hitting the road on your Vermont road trip!

Book in advance

Because Vermont isn’t super populated, there can be limited options when it comes to lodging in some areas. We suggest booking in advance to ensure that you can find a spot that fits your needs and budget, especially during peak seasons.

Download offline maps

There were a few areas where we didn’t have the best cell phone service, which can be tricky if you’re trying to figure out where to go, both on the road or on the trail. We highly recommend downloading offline AllTrails Maps and offline Google Maps so you can navigate without cell phone service and don’t get lost!

Want to get 30% off an AllTrails+ membership ? Use our code aplusk30 (you must redeem this code on the website, not the app)! We use AllTrails+ on every single hike and it is the most helpful hiking tool out there! Some of the features we love are offline maps (so we can navigate even without cell service), wrong-turn alerts, and its 3D maps feature, so we can get a feel for trails before we hike.

Almost everything is dog friendly

One of the many great things about Vermont is that it is very dog friendly! Since there are no national parks, which usually prohibit dogs, your furry friend can join you for many activities on this guide! However, there will be times that your pup will need to stay behind, such as visiting restaurants, tours, and other indoor activities, so make sure you have a safe place to leave them.

Learn how we travel with a dog and what we do with Kona when she cannot join us on our adventures.

Start early

Our #1 tip anywhere we go is to start early! While Vermont may not be as crazy busy as some national parks and other destinations we have visited, it can get crowded with tour buses (we got stuck behind a few huge bus groups). We tried to start our days early and hit the trails around sunrise and it paid off every time!

Harvest Hosts are a lifesaver for RVs!

Since we travel in a van, we typically sleep in our van at night, instead of hotels or Airbnbs. While we did stay in one hotel in Vermont, the rest of the time we tried to boondock in the area. However, boondocking out east can be pretty tricky, with very limited free public land, but thankfully there are many Harvest Hosts in the area! Harvest Hosts is a paid membership that lets you stay at farms, breweries, wineries, golf courses, and other spots for FREE, with the expectation that you will support the business. While this means you do need to spend some money and it’s not totally free, it’s usually a unique experience and you get to support a local business.  We slept at a total of 4 Harvest Hosts while in Vermont, including a cider mill, farm, golf course, and maple syrup farm. If you’re also traveling in a van or RV, we highly recommend Harvest Hosts while in the area. You can use our link to get 15% off a membership!

Be flexible!

During our time in Vermont we had two things impact our plans a bit: foggy weather and less foliage than we hoped.  We had tried hard to plan our trip so we’d hit peak foliage, but were a bit too early for most areas. It is super hard to predict foliage, as it varies year to year due to weather conditions, so if you plan to visit in the fall, prepare to be a bit flexible if the colors are not at the level you hoped. During the fall, you can likely always find an area with more vivid colors if you’re willing to drive a bit further or change plans a bit. As for the foggy weather, despite being full time travelers, we had a set amount of time in Vermont and couldn’t adjust, so we just decided to roll with the punches and embrace it, even with zero views. We still had a blast and made some fun memories!

A common question we get when sharing our adventures is what we bring with us. We have almost all of our gear listed here , but here are some items we especially recommend bringing to Vermont!

Hiking Gear

Since most of the best things to do in Vermont include outdoor activities, you’ll want to bring plenty of outdoor gear and clothing. To see everything we take hiking, as well as our favorite clothing, check out our hiking gear . 

The weather can vary in Vermont, so layers are good to have! During our trip we experienced warm sun and cold fog within days of each other, so having layers was key to staying comfortable.

Bike (if you have one)

If you have a bike and are driving to Vermont, we suggest bringing it with you! There will be multiple opportunities to ride your bike while on your road trip and while you can rent one (like we did), it would be cheaper and easier to have your own.

Now that you know a bit more about Vermont, how to get there, and other tips, it’s time to plan out your road trip! Below is our 7 day Vermont itinerary, which can of course be adjusted to what you want to do, how much you want to do in a day, and how much time you have. We have included a variety of activity options for some days, that way you can adjust it to your preferences and abilities. We have also included some add-on options if you have more time and are looking for more things to do!

Day 1: Travel to Vermont

For the first day of your Vermont road trip, head to Vermont! We suggest making it near Woodstock, Vermont, which is a cute town and is also close to Day 2 of the itinerary. If you arrive early enough, spend as much of the day as you have to explore the Woodstock area. We were unable to squeeze Woodstock into our road trip, but we had originally planned to stop there and here are some spots we had hoped to visit! 

Things do in and near Woodstock, VT

• Quechee State Park : This state park, which is just 15 minutes to the east of Woodstock, is home to Vermont’s deepest gorge, which you can experience on the 2.7 mile Quechee Gorge Trail .
• VINS Nature Center : This nature center is right by Quechee State Park and is home to a variety of birds and a very cool looking forest canopy walk!
• To see a covered bridge, visit either the Middle Covered Bridge (right in Woodstock) or Taftsville Covered Bridge !
• Sleepy Hollow Farm : This is a very popular spot to snap a photo during fall foliage. It overlooks someone’s farm, which is extremely picturesque! Make sure to be respectful, as this is someone’s property.
• Billings Farm & Museum : This dairy farm gives visitors a glimpse of what farm life is like, both in the past and the present, through different exhibits.
• Hike The Pogue and Mount Tom trail (4.2 miles, 643 feet of elevation gain) for views of Woodstock, a small lake, as well as the surrounding area.

Places to eat in Woodstock, VT

• Abracadabra Coffee
• Mon Vert Cafe
• Worthy Kitchen

Where to stay

For your first night, we suggest staying close to Woodstock or a bit closer to tomorrow’s activities in Rutland. Since you’re only going to be staying for a night, a hotel would be easiest, as most Airbnbs in the area require 2+ night stays. In Woodstock, there are no major hotel options, just local inns, which can be pricey. But a little bit east in White River Junction there is a Fairfield Inn & Suites , Holiday Inn Express , and Hampton Inn . In Rutland, there is a Hampton Inn and Best Western Inn & Suites . This will be about a 20 minute drive to tomorrow’s major activity.

Optional Add on: Day in Boston If you’re traveling by plane and landing in Boston, you could spend a day exploring a bit of Boston before heading to Vermont, which is a city we have yet to visit, but REALLY want to. 

Day 2: Tour a Maple Syrup Farm!

Watch part of our tour at Baird Farm to get a better idea of what to expect and learn some maple syrup facts!

For today’s big activity you’ll tour a maple syrup farm! Vermont is the largest maple syrup producer in the United States, with 2.22 million gallons produced last year, over half of the total production for the US. Every year, starting in late January or early February, sugaring season occurs, which is when sap is collected from trees and maple syrup is actually made. This process lasts for 4-6 weeks! Although our suggested time to visit Vermont is not during sugaring season, it’s still worth visiting a farm to learn about the process and of course try maple syrup! There are many farms to tour, but we highly recommend visiting Baird Farm , which is in Chittenden, Vermont. This is a 4th generation family farm, which originally started with cows and now makes maple syrup. And unlike most maple syrup producers in Vermont, who offer self guided tours where you can watch videos and see some equipment, Baird Farm actually takes you on a tour themselves! 

The tours are FREE and you’ll get to see their maple trees, hear the process of how sap is collected, see their equipment and learn how sap is turned into syrup, and do a tasting at the end! Our guide, Jacob, who is one of the owners, was extremely nice, passionate, and took the time to get to know our group so he could customize the tour. Plus the syrup was so delicious, both their pure maple syrup and their infused varieties!  NOTE: Baird Farm only offers tours certain days of the week at only one time slot, so make sure to book in advance. If Baird Farm is not offering tours the day of your trip, you can visit Sugarbush Farm in Woodstock and do a self guided tour. If you decide to do this, we’d suggest staying in Woodstock the night before.

What to do after your maple syrup farm tour

Assuming you go on the Baird Farm tour, we suggest heading to Middlebury (40 minutes north) for a bit on your way to Burlington for the night. While there:

• Grab lunch at either The Mad Taco or Haymaker Bun Company & the Arcadian .
• Walk around Middlebury and see the falls in town !
• Grab a maple creemee at Vermont Maple Market ! A creemee is basically an extra creamy soft serve ice cream, and while you can get creemees in a variety of flavors, maple creemees are all the rage in Vermont. They have a delicious sweet, maple (but not overpowering) taste. We LOVED them!

After exploring a little bit, drive to Burlington, which is 1 hour north of Middlebury. If you’re looking for somewhere to grab dinner, we suggest Taco Gordo , Bluebird Barbecue , Pho Hong , or Honey Road .

After day 2, we suggest staying the night in Burlington, which will put you right in the heart of tomorrow’s activities! Here are some suggestions of where to stay. Hotels: Hilton Garden Inn Downtown , Hotel Vermont , Courtyard Burlington Harbor , and Homewood Suites . Airbnbs: Beautiful Suite , The Garden Studio , Modern Rustic Backyard Cottage , Josie’s Secret Downtown Gem , and Deluxe Cute Apartment . Campgrounds: North Beach Campground

Day 3: Burlington

Watch us spend a day in Burlington, where we biked around and ate some tasty BBQ!

About Burlington

Burlington is a vibrant, welcoming, and beautiful city that is located on the shore of Lake Champlain. It is the most populous city in Vermont and is home to the University of Vermont, many local restaurants and shops, parks, and gorgeous views. 

• Start your day with coffee at Perky Planet , which is more than just a coffee shop. They have an incredible mission to break down barriers to employment for those with intellectual and developmental disabilities. Some of the things we read that they have done is insulated the ceilings to reduce the echos for their employees with hearing impairments and have implemented different technologies to make tasks more accessible. Another great option is Kru Coffee . Regardless of which you choose, we suggest taking your coffee down to the Waterfront Park to enjoy it with a view of Lake Champlain, which is 490 square miles and is the largest lake in Vermont. This lake also borders New York and Quebec in Canada and from Burlington you can even see the Adirondacks in New York across the water!
• Have breakfast at August First or Penny Cluse , which are both very popular spots for breakfast and lunch items.
• Ride bikes on the Island Line Trail , which is a 14 mile (one way) trail that goes from just south of downtown Burlington and across Lake Champlain via a causeway and bike ferry, to South Hero, Vermont. Along the trail you’ll go by different beaches and parks, see many views of Lake Champlain, and go through a residential area, before making it to the causeway, which is a narrow pathway that takes you three miles across Lake Champlain. This section of the ride is amazing, with water all around you, plus mountain views. Towards the end of the causeway there is a 200 foot gap that requires you to take a ferry to get across and continue the causeway. The ferry is seasonal and runs daily in the summer, but after Labor Day, it only runs Fridays-Sundays, until mid October. It costs a suggested $10 donation (round trip) to ride. If you do not have a bike and need a rental, we rented eBikes from Local Motion and it was a blast! Since it was a lot of miles, having the assistance of a motor was helpful. We also suggest bringing snacks or a picnic lunch to enjoy along the way!
• Head over to Shy Guy Gelato , a local, homemade gelato spot that makes some delicious flavors! They do sell out, so make sure to check their Instagram in advance!
• Walk around Church Street Marketplace , which is a 4 block outdoor pedestrian mall with shops and restaurants, cute buildings, trees, cobblestone walkways, and colorful flags hanging, all ending at a picturesque church.
• For dinner, head to either Taco Gordo , Bluebird Barbecue , Pho Hong , or Honey Road ! And if you’re a beer drinker, Zero Gravity Brewery , Switchback Brewing Co , and Foam Brewers are popular spots to check out.

For day 3, you could either stay another night in Burlington, using one of the suggestions above, or you could stay in the Waterbury and Stowe areas, which is where the next two days of your road trip will be. Here are some suggestions of where you can stay there! Hotels: Best Western Plus Waterbury-Stowe , Fairfield Inn & Suites Waterbury Stowe , Trapp Family Lodge , Green Mountain Inn , and Timberholm Inn . Airbnbs: The Coffee Roost , True Vermont Cabin , Bright & Airy Guest House , Cozy Bungalow Home , and Classic Stowe Ski Chalet . Campgrounds: Smuggler’s Notch State Park Campground , Gold Brook Campground

Optional Add on: Camel’s Hump State Park If you have an extra half day or so, we suggest visiting Camel’s Hump State Park, which is a FREE state park (with no facilities) that is named after a distinctive hump on top of the mountain that you can see from miles away. While in the park, hike the 6 mile Camel’s Hump Trail to the top! 

Day 4: Waterbury + Stowe

Watch us explore Waterbury and Stowe, including apple cider donuts, a corn maze, and a covered bridge!

About Waterbury & Stowe

Waterbury and Stowe are likely some of the most popular areas to visit in Vermont and it’s no secret why! Nestled in the Green Mountains, the towns are quaint and charming, the views are amazing, there are great local businesses, both small and large, and plenty of activities year round. The two towns are located about 15 minutes apart and connected by the Green Mountain Byway, with Waterbury more south and Stowe more north, making them easy to visit together. There are many things to do and places to eat or drink in the area, so we’re providing many options in this day’s itinerary so you can choose what you’re most interested in.

• Have a sweet start to the day with apple cider and apple cider donuts at Cold Hollow Cider Mill ! This place is so amazing and makes some insanely fresh tasting cider and donuts, both of which you can watch them make! They have a room in the back where you can learn a bit about the apple cider process and watch them work and in the front, you can see them frying up fresh donuts.  If you want something savory as well, they have a restaurant next door that serves breakfast, lunch, and hard cider. For the coffee lovers, some good coffee shops in the area are Vermont Artisan Coffee & Tea (Waterbury), Black Cap Coffee & Beer (Stowe), Woodland Baking and Coffee (Stowe), and PK Coffee (Stowe).
• Spend the morning and afternoon exploring Waterbury and Stowe! Here are some options, listed in order from Waterbury up to Stowe, which you can mix and match to plan your perfect day. Kayak on the Waterbury Reservoir : The Waterbury Reservoir is the 9th largest body of water in Vermont and was created in the 1930s by the Civilian Conservations Corps as a way to protect nearby towns from floods. There is a state park on the reservoir called Waterbury Center State Park , where you can rent kayaks and enjoy the mountain views from the water. Note: dogs are not allowed here. Visit Ben & Jerry’s : Ben & Jerry’s started in a renovated gas station in Burlington, Vermont in 1978 and today its factory and headquarters are located in Waterbury. They offer factory tours (currently closed until sometime in 2022), ice cream by the scoop, and even a flavor graveyard where you can see flavors from the past, with headstones. See the Gold Brook Covered Bridge: There are 104 covered bridges in Vermont, the highest density of covered bridges in the US, which were originally created to protect bridges from the harsh New England weather. Today they make for beautiful photo opps and a popular covered bridge between Waterbury and Stowe is the Gold Brook Covered Bridge , also known as Emily’s Bridge because of a very sad story of a girl named Emily who hung herself from the bridge after her lover that she was supposed to elope with never showed up. Hike up to the Stowe Pinnacle Overlook: Just down the road from the Gold Brook Covered Bridge is the Stowe Pinnacle Trail , which is 3.7 miles and 1,604 feet of gain (so it’s pretty steep!) and takes you to an overlook with views of the Green Mountains. Walk around Stowe: When we think of a classic New England town, we think of Stowe. The town is tucked in the mountains, has beautiful Colonial style buildings, and an iconic New England church steeple. It’s a great place to walk around, shop a bit, and has some good spots if you need lunch, a sweet treat, or beer. Here are some spots to check out: Grab a sweet treat at Laughing Moon Chocolates . Grab lunch or beer at Idletyme Brewing Company . Tour The Alchemist Brewery , which is currently only offering daily tours at 5 PM. Bike the Stowe Path: A popular thing to do in Stowe is to go on the Stowe Recreation Path . This is a 5.5 mile (one way) path that takes you through Stowe and by farms and restaurants. This pathway is best on a bike, but we enjoyed walking Kona on part of the path as well! Get lost in a corn maze: If you visit in the fall, make sure to check out the Percy Farm Corn Maze . Every year Paul Percy mows a unique maze in his farm’s corn field, which costs $8 per adult (cash or check only), for visitors to try to conquer. We found it to be trickier than expected and it took almost an hour to get out! Chase some waterfalls: The Stowe area is home to a handful of beautiful waterfalls. We hiked to Moss Glen Falls , which is only about 0.25 miles from the trailhead (parking is pretty limited) and takes you to a gorgeous, multi-tiered waterfall. Another popular option in the area is Bingham Falls , which is a 0.5 mile round trip hike!
• Have dinner at Piecasso , which is a delicious pizza spot in Stowe (we loved it!). A couple other options are Idletyme Brewing Company , von Trapp Brewery and Bierhall (the family from the Sound of Music!), or Trattoria La Festa , an authentic Italian spot.

We suggest staying in Waterbury or Stowe again for this night!

Day 5: Mount Mansfield

Watch us hike to the top of Mount Mansfield on a foggy day!

About Mount Mansfield

Mount Mansfield is the tallest point in the state of Vermont at 4,393 feet. The mountain is known for looking like someone laying down and different portions of the mountain are named after different features, including the forehead, nose, upper and lower lips, and the chin, which is the summit. 

How to get to the top of Mount Mansfield

There are three main ways to get to the top of Mount Mansfield: hiking, driving, or a gondola. Hiking (our top pick!): If you choose to hike to the top of Mount Mansfield (which is what we did), there are tons of trail options, but we suggest the Mount Mansfield Loop , which is 7.3 miles and gains 2,880 feet. This trail starts at Underhill State Park ($4 per adult fee), which is about 45 minutes to 1 hour from Waterbury and Stowe. If you go this route, we suggest taking the Maple Ridge Trail up and Sunset Ridge Trail down, as the Maple Ridge Trail has two trickier spots, including a gap to jump and a rock wall you have to climb up, which is easier going up than down. We show these spots in better detail in this video and these spots can be tricky with a dog, but we were able to get Kona through them safely. You can also hike up and down the Sunset Ridge trail, which is still steep and rocky, but has less tricky spots. Despite us having ZERO views at the top, we had a blast hiking this trail, as it offered some challenges along the way to keep things interesting! We suggest arriving early, as parking can get full on a busy day, as can the summit, since there are many ways to get to the top. Driving: To drive up Mount Mansfield you’ll take the Auto Toll Road , which costs $29 per car + $11 per passenger. The road takes you to 3,850 feet, where you can either enjoy the views from there, or continue on the Long Trail for about 1.25 miles each way. Note: RVs and campers, bicycles, motorcycles, or dually trucks are NOT allowed on this road. Gondola: The final way to the top is to ride the Stowe Mountain Resort Gondola , which costs $37 per adult and $26 per child for the ride up and down the mountain. Once off the gondola, you can take the Cliff Trail to the Long Trail to the summit for under 1 mile each way. 

What to do after Mount Mansfield

After making it to the top of Mount Mansfield, we suggest driving the Smugglers Notch Scenic Drive (Route 108) back towards Stowe, which goes through the forest and has unique rock outcroppings. Once back in Stowe, grab food at one of the spots we shared on day 4 and if you have more time, do any other activities listed on day 4 that you didn’t have a chance to check out!

For day 5 you could either stay in Waterbury or Stowe one more night or head towards your final destination in Vermont, the Northeast Kingdom, which is under 1.5 hours from Stowe. This will give you an early start for your final day! If you choose to stay closer to the Northeast Kingdom, here are some options: Hotels: Comfort Inn & Suites Near Burke Mountain Airbnbs: Cozy Cottage in the Northeast Kingdom , Waterfront Lake House on Crystal Lake , and Remodeled 2 bedroom + loft lakefront cottage Campgrounds: Whitecaps Campground , Will-O Wood Campground , Belview Campground , and Kingdom Campground

Optional Add on: Montpelier If you have an extra day or afternoon, head to Montpelier, which is the capital of Vermont! Montpelier is a charming town and we suggest walking around the historic downtown area, seeing the state capitol building , which is beautiful, and grabbing a maple creemee at Morse Farm Maple Sugarworks !

Day 6: Northeast Kingdom

Watch us explore the Northeast Kingdom, including two epic hikes! And to learn more about our favorite hikes in the area, read our Mount Pisgah and Bald Mountain guides!

About the Northeast Kingdom

The Northeast Kingdom (abbreviated NEK) is an area in northeast Vermont, which got its nickname from a former US Senator and governor, George Aiken, who loved the area and thought it should be a kingdom. And we couldn’t agree more…it is magical! The Northeast Kingdom is home to small towns, forests, farmland, mountains, and beautiful Iakes, including Lake Willoughby, which is the second largest lake in the state and looks like a mini Norwegian fjord. This region of Vermont was our absolute favorite and we highly recommend the trek up there, especially if visiting during fall foliage.

• Get an early start and hike up Mount Pisgah (4.1 miles round trip, 1,653 feet of elevation gain), which has phenomenal views of Lake Willoughby from a few different viewpoints. It is relatively short, but steep, and it can get busy, so we recommend starting around sunrise if you can. You can learn more about the hike, including what to expect and photos from the different viewpoints in this guide .
• Spend the rest of the morning hanging out at Lake Willoughby! Lake Willoughby has two beaches, with the North Beach being much larger and more of a “lay out” kind of beach, while the South Beach is more of a cove for boats, but in our opinion has the better view. There is also a clothing optional cove near South Beach. If you want to kayak on the lake, White Caps Campground offers rentals to the public, as does Clyde River Recreation , which is located north of the lake, but they can drop off the kayaks for you!
• Grab lunch at The Parker Pie Company , which is about 25 minutes away from Lake Willoughby.
• End the day with a late afternoon or sunset hike up Bald Mountain (4.2 miles round trip, 1,463 feet of elevation gain), which takes you to an old fire tower, with incredible 360º views at the top. We share more about the hike, including more information about the fire tower in our Bald Mountain guide!

For your final night, you can either stay in the Northeast Kingdom to make the trek closer to Boston for your flight, or continue on to wherever your adventures take you next! 

Day 7: Travel back home

And now for the worst part of the trip…leaving Vermont. 🙁 For your final day, either head back home or continue your adventures. We highly recommend squeezing in some time in New Hampshire’s White Mountains if you have time, which is close to the Northeast Kingdom.  If you do head that way, check out these guides:

We hope you enjoy visiting Vermont as much as we did! We went into the state with pretty high expectations after years of anticipation and it truly exceeded them all. If you do make it to Vermont and use this guide to help with your trip, let us know! We’d love to hear about the memories you make in Vermont too!

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4 thoughts on “ 7 day vermont road trip itinerary ”.

Great post! I appreciate that you are moving at a fast pace here. Most Vermont itineraries are too slow for my liking 😉

Thank you Paula! We are glad you like the pace. We try to cater to those who have limited time, but want to see as much as they can!

I’m so excited that we are heading to Vermont next month! I’m usually the “itinerary maker” so I very much appreciate the helpful information in your videos and blog. We are a little older than the two of you so it is wonderful to get an idea of the terrain of the hikes as we can be best prepared! We would have missed out on Black Elk Peak in South Dakota had we not watched your video so a big “thank you” for that!

We are so glad to help you plan your own trip easier! Black Elk Peak is still one of our favorites!

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The Perfect Vermont Route 7 Road Trip: A 5-Day Itinerary

By Author Tara Schatz

Posted on Published: March 6, 2023

Categories Vermont , Destinations , New England USA , road trips , United States

Historic New England towns. Awesome swimming holes. Cute farm stands. And cows – lots and lots of cows. Vermont’s Route 7 travels 176 miles from Pownal in the south to Highgate on the Canadian border in the north.

This mostly rural stretch of pavement makes for a fabulous and scenic road trip, full of natural beauty, fun towns, and interesting attractions. We’ll start in the historic town of Bennington and bring you north as far as Burlington. 

If you have more than five days to spend on your road trip, I highly suggest continuing on and heading north to the Lake Champlain Islands, which are worthy of their very own weekend getaway!

If you’ve got five days, you can take a leisurely journey up Route 7 in Vermont, but you can also do this trip over a long weekend. We’re proponents of slow travel, when possible, but three days in Vermont is better than zero! 

Our Vermont Route 7 itinerary covers all of our favorite things: lovely walks and rambles, fun historic sites, local food and drink, and even a few awesome places to take a summer dip. 

So, start making your Vermont road trip playlist and packing the car, because this is a road trip you won’t want to miss.

We’re going to begin our Route 7 road trip in Bennington and head north on Route 7 to Burlington. Feel free to flip this itinerary around if you want to start in Burlington and head south. Not only is Bennington my hometown, but it’s just an hour from Albany International Airport and within four hours of both Boston and NYC. That makes this road trip a great getaway for just about anyone living in the Northeast!

Table of Contents

Day 1: Explore Bennington, Vermont

Today you’re exploring the beautiful and historic town of Bennington, Vermont. In Bennington, you can tour Vermont’s tallest building, visit the grave of a famous poet, and enjoy a fabulous meal on Main Street before turning in for the night. Driving time: Depends on where you’re coming from.

Explore the Old Bennington Historic District

Bennington is a small town (population 15,000) with a walkable downtown and historic sites dating back to the Revolution. Start by exploring the village of Old Bennington, which is listed on the National Register of Historic Places. 

If you park your car at the Bennington Battle Monument , you can explore the rest of Old Bennington on foot. Not only is the Bennington Battle Monument Vermont’s tallest man-made building, but it is also our most-visited state historic site. 

The Monument was completed in 1889 to commemorate the Battle of Bennington, which took place on August 16, 1777, during the Revolutionary War. 

Between May 1st and October 31st, you can ride to the top of the Monument in an elevator for spectacular views of the surrounding countryside. The Bennington Monument and gift shop are currently open between Thursday and Monday, from  9 am to 5 pm. 

Next, stroll down Monument Avenue past many Revolutionary War Era homes and on to the Old First Church , which was the first gathered church in Vermont. Although the lovely church that stands there now isn’t the original, it’s been around since 1805.

Behind the Old First Church, you’ll discover one of the oldest cemeteries in Vermont. Many of the gravestones here provide stellar examples of historic death imagery that was popular during the late 1700s. Robert Frost, Vermont’s most famous poet, is buried here, along with his family. Follow the signs to his grave, you can’t miss it.

Read Next: 7 Beautiful Spots to Visit in Bennington, Vermont

Lunch: Madison Brewing Company

428 Main Street, Bennington, Vermont

When we want casual fare and locally crafted beer at decent prices, we head to Madison Brewing Company on Main Street in Bennington. The food is reliably good, the atmosphere is friendly, and the service is great. They have several vegetarian options, which I appreciate, and good burgers, which Eric loves. 

The beer menu changes with the season, but you can always get our favorite, Old 76, which is an English Yorkshire-style ale. It’s very malty and strong – perfect for a fall road trip. In the summer, I almost always get the IPA.

Bennington Museum

With a strong focus on Vermont history and art, Bennington Museum includes a huge treasury of cultural artifacts and works of art, including the largest public collection of Grandma Moses paintings in the world.

Grandma Moses lived just over the border in New York and was a self-taught folk artist who began her painting career when she was 78 years old. She is a local legend in these parts and experienced critical acclaim across the country during her lifetime and beyond.

Permanent collections include several galleries of fine and modern art, a textile gallery including one of the oldest American flags in existence, and an eclectic mix of special exhibitions.

Bennington Museum has variable hours, depending on when you visit. Between June and October, it is open every day except Wednesday , from 10 am to 4 pm.

Dinner: The Miller’s Toll

716 Main Street, Bennington, Vermont

We have never had a bad meal at The Miller’s Toll , although we wish that they were open more often! The Miller’s Toll offers the best cocktails around, as well as small plates, wood-fired flatbread, and lots of vegetarian options. It’s small, dark, and bistro-like, with outdoor dining in the summer.

The Miller’s Toll is open Thursday – Saturday, from 5-9 pm.

Where to stay in Bennington, Vermont

You’ve got several choices for lodging in Bennington, depending on what you’re looking for. Here are our top picks from budget to luxury:

• Upscale:   South Shire  has nine delightful rooms housed in a beautiful Victorian home within walking distance of town.
• Budget: The Harwood Hill . This lovely motel boasts one of the best views in Bennington. The rooms and the grounds are decorated with art from local artists, and they host an artist-in-residence each season. The rooms are comfy and beautifully decorated.
• Camping: If you want to pitch your tent or park your RV, definitely head east on Route 9 to Woodford State Park, where you’ll find waterfront camping, swimming, and kayak rentals. 
• Vacation rental: Need more room to spread out? Our extended family rented this renovated barn just outside of Bennington one winter and loved it. It’s very Vermonty, with lots of room for the whole family. 

Day 2: Bennington to Manchester

This section of Route 7 is only 23 miles, so take your time. There are actually two Route 7s between Bennington and Manchester. Route 7A was the original Route 7, traveling through several small towns en route to Manchester.

A larger two-lane freeway was eventually built so vehicles could travel at 55 mph and those small towns were bypassed. We call the two roads Big 7 and Little 7. For this trip, we’re hopping on Little 7 (7A) so you get the full Vermont experience. Driving distance: 23 miles

Breakfast: The Blue Benn

314 North Street, Bennington, Vermont

The Blue Benn Diner is an institution in Vermont and a must-visit when you’re in Bennington. The diner closed for a brief spell in 2020, and for a while, we all worried that it was done for. Fortunately, new owners quickly stepped in to keep it running.

This is a classic diner car, built in 1948, and complete with table-top jukeboxes and lots of items on the menu. Get there early so you don’t have to wait!

I recommend any of the creative omelets, especially the Mexican, but you also can’t go wrong with blueberry pancakes and real Vermont maple syrup!

The Blue Benn is open seven days a week from 6 am – 2 pm .

Covered Bridge Tour of Bennington County

As you head north on Route 7A through Bennington’s shopping strip, take a detour onto Route 67A to visit three covered bridges in Bennington and North Bennington. All three covered bridges cross the Walloomsac River, and they are all within a few miles of each other. You can easily view all three covered bridges in less than an hour. Here’s a quick overview. 

Silk Road Covered Bridge, Bennington, Vermont

The Silk Road Covered Bridge carries Silk Road over the Walloomsac River in Bennington. It is the first in a series of Walloomsac River bridges that are all located within two miles of each other in Bennington and North Bennington.

A bridge has spanned the Walloomsac in this location since 1790, but the current Silk Road covered bridge was built in 1840. It is the oldest covered bridge still standing in Bennington County. This is a single-span Town Lattice Truss built by Benjamin Sears, who was a prominent builder at the time.

There is a small pull-off on both the north and south side of the bridge, with short trails down to the river for better views.

Paper Mill Village Bridge, Bennington, Vermont

The current Paper Mill Covered Bridge was built in 2000 and is a replacement of the original that was built in 1889. This is a Town lattice truss spanning 122 feet along Murphy Road. The Paper Mill Covered Bridge is similar in design to the Silk Road Bridge and is the longest covered bridge in Bennington County.

The site was home to one of Vermont’s first paper mills, and the dam below the bridge provided hydroelectric power to fuel industry in the community.

The area to the north of the Paper Mill Covered Bridge is private property. On the south end of the bridge, there is a small parking area. A short trail on the west side leads to multiple viewing sites with good views of the dam and the bridge. This is also a great spot to go fishing!

Burt Henry Covered Bridge, North Bennington, Vermont

The location where the Burt Henry Covered Bridge spans the Walloomsac River has been an important crossing since early colonial times. The original covered bridge was a double-span, built in 1840, but was entirely replaced as a single-span in 1989. This is a Town lattice truss bridge that carries River Road for 121 feet across the Walloomsac.

Park in the small parking area just north of the entrance to the bridge. Of the three covered bridges in Bennington, the Burt Henry Covered Bridge provides the best access. It’s a great spot for picnicking, fishing, and cooling off (but it’s still not deep enough for swimming).

Arlington Green Covered Bridge, Arlington, Vermont

Now it’s time to leave Bennington behind and head north. Continue on Route 67A and then turn left on Route 67 until you get to the junction of 7A. From here, you will drive north through Shaftsbury and into the town of Arlington.

The painter Norman Rockwell, who is famous for so many scenes of New England life, made a home with his family in Arlington for 14 years. Take a short detour off of 7A and head east on Route 313 when you get to Arlington. In about four miles, you’ll come to the Arlington Green Covered Bridge. 

Drive through the bridge and park your car on the other side. The Arlington Green Covered Bridge is the most photographed bridge in Vermont. This is also a great spot to take a dip underneath if the weather is cooperating. After taking in the pastoral views, stroll down the road a piece to Rockwell’s Retreat, a historic inn that was built in 1792.

The view of the bridge from in front of the inn is the very same that Norman Rockwell enjoyed in the decade he lived here from 1938 to 1953.

Read Next: Explore the Covered Bridges of Bennington County, Vermont

Lunch: Amy’s on the Road

4361 Main Street, Manchester, Vermont

Amy’s on the Road is a food truck sensation, serving locally sourced meals out of an Airstream. Find Amy’s next to Mother Myrick’s Confectionery (perfect for dessert) on Main Street. Sit outdoors, enjoy some live music (if you’re lucky), and indulge in a fried chicken sandwich or a homemade veggie burger.  

Amy’s on the Road is open Monday – Saturday 8 am – 2:30 pm and closed on Sundays.

Northshire Bookstore

4869 Main Street, Manchester, Vermont

You can’t visit Manchester without popping into my favorite bookstore! The Northshire Bookstore on Main Street is an institution, with enough books to make your head spin, including a great used book section, a music section, and a fabulous floor dedicated to children’s books, games, and puzzles.

If you’re a book lover, a visit to Northshire Bookstore is an absolute must! And if you love shopping, you should probably spend the rest of the day meandering around Manchester, which is known for its outlet stores and boutique shopping.

Northshire Bookstore is open daily from 10 am – 7 pm.

Two Options for an Afternoon in Manchester, Vermont

Because there’s a lot to do in this little town, I’m giving you two options for spending your afternoon in Manchester, Vermont. 

Option One: Explore Mt. Equinox

Want to work up a sweat and get outdoors? I recommend hiking to the top of Mt. Equinox in the Equinox Preserve. The Equinox Preserve consists of over 914 acres on the slopes of Mt Equinox, and there are numerous hikes for all abilities.

If you want a leisurely stroll in the woods, hike the loop around Equinox Pond (.75 miles). For a serious workout to the summit of Mt. Equinox, hike 6.2 miles (round-trip) up a steep trail with 2,840 feet of elevation change. Mt. Equinox is the tallest mountain in the Taconic Range at 3,855 feet. Find trail descriptions and a trail map at Equinox Preserve Trust . 

If you want the amazing view from the summit of Mt. Equinox, but don’t want to put in the work, you can also drive to the top on Mount Equinox Skyline Drive . So many choices!

Option Two: Southern Vermont Arts Center

93 SVAC Drive, Manchester, Vermont

Located on 120 acres on the side of Mt. Equinox, Southern Vermont Arts Center includes numerous galleries that feature more than 1,000 works from regional artists in their permanent collection, as well as a rotating collection of special exhibitions and the largest outdoor sculpture park in Vermont. 

A tour of the grounds and galleries is an inspiring way to spend the afternoon, and there’s even a cafe if you need some extra nourishment. We especially love the woodland trails and outdoor sculptures!

Southern Vermont Arts Center is open Tuesday – Sunday 10 am – 5 pm.

Dinner: Seasons

4566 main street, manchester center, vermont.

We love the outdoor seating area at Seasons in Manchester, so if you’re traveling during the summer or fall, we definitely recommend it! The maple-roasted pear and arugula salad is great if you want something light, and they also have a unique selection of sandwiches and burgers. I hear the fish tacos are awesome too!

Seasons is open Tuesday to Thursday from 5 pm – 8:30 pm, Friday and Saturday from 5 pm – 9 pm , and Sunday from 12 pm – 4 pm.

Where to Stay in Manchester

• Luxurious : Built in the 1880s, the Inn at Manchester is a historic bed and breakfast on four landscaped acres, but within walking distance to the town’s historic district. Beautifully appointed guest rooms all have modern comforts and luxurious linens. Children over 13 are welcome. 
• Budget: Manchester View is a cozy motel-style inn with an outdoor pool, farmhouse decor, and rooms with fireplaces. Breakfast is included.
• Camping: I f you plan on camping, head north out of Manchester to Emerald Lake State Park . This beautiful lake provides some of the west swimming in Southern Vermont, and there’s a nice hiking trail around the lake as well. 
• Vacation rental: Need more room to spread out? This historic, dog-friendly vacation rental is located right in town and sleeps four at an affordable price. 

Day 3: Manchester to Middlebury

Continuing north on Route 7, today takes you on a few outdoor adventures and an exploration of the historic city of Rutland and its fabulous murals. Total driving time: 78 miles

Breakfast: Up for Breakfast

4935 Main Street, Manchester, Vermont

Start the day off right at the bustling Up for Breakfast (cash only) on Main Street in Manchester. Treat yourself to the french toast with real maple syrup and a side of local sausage. Might as well overdose on the maple goodness with maple lattes too!

Up for Breakfast is open from Monday through Friday from 7 am – 12:30 pm and Saturday and Sunday from 7 am – 1:30 pm.

Check out the Incredible Murals in Rutland, Vermont

For years, Rutland has been known as a no-nonsense, working-class city with a cute historic district and a history as one of the world’s leading producers of marble. But, Rutland has an up-and-coming art scene that is worth checking out.

Not only is the downtown area home to five unique art galleries, but downtown Rutland has also commissioned 15 larger-than-life murals that have been painted on historic buildings and walls throughout the city.

Park your car in downtown Rutland to explore the murals and the downtown area.

Lunch: Roots Rutland

55 Washington Street, Rutland, Vermont

Roots is a gem of a restaurant in Rutland with an eclectic menu from minimally processed, locally grown food. Although the menu changes with the seasons, we’ve always had the good fortune of a stellar dining experience. There are a lot of amazing vegetarian options too! Current favorites include fried Brussels sprouts, which I can never turn down, and the pan-seared tofu served over Chermulla beet & potato hash with spinach & roasted garlic aioli. Yum! 

Roots Rutland is currently open from 11:30 pm to 8 pm, Monday through Saturday.

Taconic Mountains Ramble State Park

After lunch, take a quick detour off of Vermont Route 7 to one of my all-time favorite Vermont State Parks. Vermont’s newest state park is appropriately named — Taconic Mountains Ramble State Park is a unique collection of hiking trails meandering over 204 acres of fields, forests, gorges, cliffs, and gardens. 

This is an undeveloped park with no amenities, but it is worth visiting for the stellar views, the cool Japanese gardens, and the fun/challenging trails. Find out why we love Taconic Mountains Ramble State Park and then put it on your itinerary! Give yourself a few hours to explore here.

Dinner: Fire and Ice

26 Seymour Street, Middlebury, Vermont

From Taconic Mountains Ramble State Park, drive north on Route 30 for about 25 miles until you get to Middlebury, which you’ll be exploring tomorrow.

Fire and Ice is a uniquely decorated restaurant with delicious food – mostly steak and seafood, but there are a few nice vegetarian options as well. They’ve been a Middlebury institution for almost four decades! Eat in the cozy dining room or outdoors on the patio, but be sure to make reservations ahead of time. Oh, and for dessert, get the Vermont Mud Pie!

If you are looking for more casual fare, the attached Big Moose Pub has a tavern menu and bar seating. Fire and Ice is open for dinner Wednesday through Friday from 4 – 8 pm, and lunch on Saturdays and Sundays starting at noon.

Where to Stay in Middlebury, Vermont

• Luxurious: Swift House Inn is located just two blocks from downtown in a former governor’s mansion on four acres of land. The upscale rooms are spread across three historic homes.
• Budget: I have always wanted to stay at Middlebury Sweets Motel , which is a budget-friendly motel with a candy theme! You’ll find Middlebury Sweets on the property – the largest candy store in Vermont! 
• Camping: Rivers Bend Campground provides waterfront camping with full hook-ups and an outdoor pool in nearby New Haven. It’s one of the very few private campgrounds we recommend. 
• Vacation rental: Need more space? Rent this three-bedroom home within walking distance to downtown Middlebury. It’s pet-friendly and includes a fully-stocked kitchen.

Day 4: Middlebury to Shelburne

Today you’ll explore Middlebury and then drive north to Shelburne. As you drive north on Route 7, you’ll finally get a glimpse of our beautiful Lake Champlain, which is 124 miles long and covers 490 square miles! Lake Champlain is the sixth largest lake in the US, after the five Great Lakes.

Be on the lookout for our loveable lake monster, Champ, who is said to be a cousin of the Loch Ness Monster. Total driving time: 29 miles

Breakfast: Otter Creek Bakery

14 College Street, Middlebury, Vermont

Whether you want to relax with a croissant and a cup of coffee or go all out with a breakfast pizza, you can do it at Otter Creek Bakery. Great outdoor seating, and delightful coffee drinks. It’s centrally located on College Street.

Otter Creek Bakery is open from 7 am – 2:30 pm from Monday through Saturday, 7 am – 4:00 pm

After breakfast, take some time to stroll around downtown. Pop into a few shops and check out the view of Middlebury Falls. 

UVM Morgan Horse Farm, Weybridge, Vermont

Did you know that the Morgan horse is one of the earliest horse breeds developed in the United States and that it is the state animal of Vermont? I’ve been visiting the Morgan Horse Farm ever since I was a kid and read Justin Morgan Had a Horse by Marguerite Henry. This is a working horse farm that was created in 1907 to improve the breed. In 1951, it was transferred to the University of Vermont. 

Take a tour of this beautiful farm and learn about the history of the Morgan horse. The views alone are worth the trip, but the horses make it extra special! Advanced registration for tours is currently required. 

Read Next: 95+ of the Best Things to Do in Vermont

Lunch: 3 Squares Cafe

141 Main Street, Vergennes, Vermont

3 Squares Cafe is a casual, eclectic cafe in Vergennes Vermont, which you’ll drive through on your way to Shelburne.

Follow the signs to Vergennes as you’re driving on Route 7 and make the left-hand turn into town. You can’t miss it! While you won’t have time to explore Vergennes with this itinerary, I recommend giving more than a drive-by if you have time.

3 Squares has been around for at least a decade, and it’s one of our favorite stops when we’re road-tripping on Route 7. They’ve got a fun selection of hot sandwiches, burgers, and vegetarian options, and a great atmosphere inside and out. 

3 Squares is open Thursday to Monday, from 8 am to 3 pm.

Relax and Rejuvenate at Shelburne Farms

Shelburne Farms is one of my favorite places in the world.

Not only is it a beautiful working farm, but the views are beyond incredible, there are lots of walking trails, and you can spend the night! We have visited Shelburne Farms for kids’ programs and for lots of special events, but it’s such a great destination to just unplug and soak up the Vermont vibes. 

Your next few days will be very busy exploring Shelburne and Burlington, so for this afternoon, I’m advocating that you take it easy and spend the rest of the day, dinner, and night at Shelburne Farms.

Dinner: Folino’s Wood-Fired Pizza

6305 Shelburne Road, Shelburne, Vermont

Folino’s makes the best wood-fired pizza we’ve ever had in Vermont. The slightly charred, crispy crust is so yummy, and you can get fun combinations of toppings.

Another bonus: Folino’s is BYOB, and is located right next door to Fiddlehead Brewing Company, making this a great stop for craft beer lovers! 

Folino’s is open Sunday through Thursday from 12 pm – 8 pm , and Friday and Saturday from 12 pm – 9 pm.

Where to Stay in Shelburne, Vermont

• Luxurious: The Inn at Shelburne Farms is a special treat if you can get a room. Be sure to watch the sunset over Lake Champlain!
• Budget: Days Inn Shelburne is a budget-friendly motel with clean rooms and a nice outdoor pool. It is just north of the village. 
• Camping: Mt. Philo State Park is such a gem! It’s about eight miles south of Shelburne with just a handful of sites. This is a beautiful spot to watch the sunset and the campsites are really quiet. 

Day 5: Shelburne To Burlington

Today you’ll be exploring the renowned Shelburne Museum and then heading north to Vermont’s biggest city. Total driving time: 8 miles

Breakfast: Rustic Roots 195 Falls Road, Shelburne, Vermont

Ready to fill up on some seriously good eats before today’s adventures? Rustic Roots is a chef-owned restaurant serving delectable breakfast and lunch on the village green in Shelburne. Patio seating is available and breakfast and lunch are both served all day. The breakfast sandwiches and popovers are my two favorites, but the menu has all kinds of goodies, so bring a big appetite!

Rustic Roots is open from Wednesday through Sundayy from 9 am – 2 pm.

Explore the Shelburne Museum

I’ve been visiting Shelburne Museum since I was a kid so there’s a lot of nostalgia attached to my visits, but I’ve also brought first-time visitors and everyone agrees that it is one of the best museums in Vermont. 

The collections at Shelburne Museum are an eclectic mix of historical artifacts, folk art, circus pieces, textiles, and other interesting bits of Americana. Galleries are spread across 39 historic buildings on 45 beautifully landscaped acres.

As a kid, I especially loved hopping aboard the Ticonderoga steamboat, which roamed Lake Champlain from 1906 until 1953. I loved that such a huge boat was parked on the museum lawn and that I could actually climb on board to see what it would have been like in 1923. 

While the Ticonderoga will surely be a favorite for you too, you can also visit a covered bridge, a jailhouse, a locomotive, a huge round barn, a blacksmith shop, and a lighthouse. You can spend a full day at the Shelburne Museum, and we wouldn’t blame you a bit if that’s what you decide to do! 

Insider tip: If you do decide to spend the day at the museum, you can get window take-out service at Weathervane Cafe. The menu is pretty basic, but they do have soup, sandwiches, and ice cream, which is more than enough. 

Rent Bikes and Explore the Bike Path in Burlington

Assuming you had lunch at the museum, your next stop will be Local Motion to rent bikes for the afternoon.

If you haven’t eaten, you will find lots of eateries on Church Street, which is a pedestrian-only shopping area. Public parking is available on the street or at a number of parking garages around town (just follow the parking signs).

Local Motion is a nonprofit organization that advocates for active transportation and safe streets. It’s located right on the Burlington bike path along Lake Champlain. At Local Motion, you can rent regular bikes, tandem bikes, child bikes and trailers, and E-bikes. You should reserve your bikes ahead of time so that you don’t miss out. 

Once you have your bike rental, head north on the Burlington Greenway (bike path), which runs for 14 miles along Lake Champlain. You will see lots of places to stop and explore on your journey, including the Burlington waterfront and a few small beaches.

Here’s a trail map to help with planning.

Anywhere along the bike path makes the perfect sunset spot, so if you have your bike rental for more than a single day, definitely take advantage!

Dinner: Honey Road

156 Church Street, Burlington, Vermont 

There are a lot of great restaurants in Burlington, and it was so hard to choose a favorite spot to recommend, but I’m going with Honey Road because I’ve been craving their small plates and cocktails for months. If you can’t get a table at Honey Road, reach out and I’ll try and recommend something else. 

I’ve been pretty much obsessed with Honey Road since they opened a few years ago. Featuring Eastern Mediterranean cuisine in a small, but bustling restaurant, Honey Road is one of the top-rated restaurants in Burlington and 100% worth the effort it takes to get a table.

If you think of it, reserve several days in advance, so you don’t miss out. Small plates make it easy to mix and match your meal with your travel companions, which also means you can try more food!

Honey Road is open for lunch and dinner between Sunday and Thursday, 4 – 9 pm, and Saturday and Sunday from 4- 10 pm.

Enjoy Nightlife in Burlington

Up until now, you’ve been driving through rural Vermont and enjoying small villages and outdoor recreation, but Burlington is our big city and it has real nightlife! If you’re craving a night on the town, tonight is your chance!

While I can’t predict what the music scene will look like during your trip, here are some great spots to imbibe. Pick up a copy of Seven Days when you get into town for a taste of what’s happening while you’re there. Here are some of the local hot spots.

• The Archives: Beer, cocktails, and vintage arcade games are exactly what you’ve been looking for. 
• ArtsRiot: Indoor/outdoor seating, great cocktails, a robust food menu, and art. What more could you ask for?
• Red Square: Known for its robust drink menu, live music, and DJs, Red Square is perfect for late-night adventures!
• Three Needs Taproom: A Burlington staple for decades now, the Three Needs is the place to go for craft beer and cocktails, a game of pool, and cozy outdoor seating. This gem of a place is not to be missed!

Where to Stay in Burlington, Vermont

You have a lot of choices for lodging in Burlington. While I recommend staying somewhere within walking distance of downtown, those choices are a bit on the pricey side. I’ve included a favorite motel in Colchester if you want a budget option.

• Luxurious: Hilton Burlington Lake Champlain has gorgeous views of the lake and is within walking distance of Church Street, shopping, restaurants, and nightlife.
• Budget: Starlight Inn is actually in Colchester, a few miles outside of Burlington, but it’s right next to the drive-in movie theater and all the rooms have a movie theme. We are huge fans of quirky motels and this one is awesome!
• Camping: You can actually camp right in the city at North Beach, right on the bike path. Sites are not secluded, but this is a great way to stay on the water for an affordable price. 
• Vacation rental: Need more room to spread out? This historic home on VRBO sleeps six and is within walking distance of downtown. It’s got three bedrooms, a full kitchen, and two parking spots. 

Read Next: The Best Things to do in Burlington, Vermont in the Summer

Day 6: More of Burlington

Got an extra day? Explore more of Burlington! On your bonus day, you’ll explore more of Lake Champlain and learn more about its ecology and history. There will be time for ice cream, shopping, and great food as well! Total driving distance: 0 miles

Breakfast: The Grey Jay

135 Pearl Street, Burlington, Vermont

This is not your ordinary breakfast joint! The Grey Jay on Pearl Street makes the most delectable baked goods and fantastic Mediterranean-inspired breakfast and lunch items. The menu is an eclectic mix of breakfast and lunch specialties with lots of vegetarian options.

The Grey Jay is open every day from 9 am-2 pm.

Get Out on the Water at the Community Sailing Center

Explore Burlington Bay in a human-powered watercraft. At the Community Sailing Center, you can rent kayaks, canoes, or paddleboards, and even book a private lesson if you need it. Want to try sailing? You can book a private lesson for you and your family aboard a boat from their fleet of sailing vessels.

This is a great way to see Burlington from a whole new perspective, and it’s the perfect way to get out on the water, especially in the summer! Learn more about renting a boat at the Community Sailing Center. 

Lunch: August First

149 S. Champlain Street, Burlington, Vermont

August First, located on the corner of S. Champlain and Main Street, is known for its crazy-delicious baked goods, especially maple biscuits! I have had many a relaxing cup of coffee at August First, but I’ve only recently discovered their lunch menu.

There are lots of vegetarian options, including my current favorite, the ramen noodle salad, which consists of chilled noodles, a jammy egg, and veggies with the yummiest sesame tamari dressing. The space is a renovated garage and the atmosphere is very cozy-industrial. 

August First is open seven days a week from 7:30 am – 3 pm.

Spirit of Ethan Allen

You’ve already done a bit of exploring on Lake Champlain, but hopping aboard a cruise ship for a narrated boat ride is a great way to learn about the history, geology, and ecology of the lake. The Spirit of Ethan Allen provides fun narrated cruises, and you can buy beer and refreshments for relaxing on the deck. Dinner cruises and sunset cruises are offered too. 

In my opinion, this is one of the most relaxing ways to spend your last afternoon on Lake Champlain. You’ll be treated to fantastic views of the Burlington waterfront as well as the Adirondack Mountains in New York and the Green Mountains east of Burlington.

Dinner: A Single Pebble

133 Bank Street, Burlington, Vermont

Tonight’s dinner is upscale authentic Chinese made with the freshest ingredients served family-style. A Single Pebble is a treat, whether you’re in the mood for seafood, beef, or a completely vegetarian meal, a Single Pebble prepares everything from scratch for a delectable meal like you’ve never experienced.

A Single Pebble is currently open from Tuesday through Saturday, starting at 4:30 pm. Reservations are suggested

Vermont Route 7 Road Trip FAQs

We get a lot of questions about traveling through Vermont, so we just wanted to take some time to answer the ones we get most often. If you have any other questions about road-tripping in Vermont, simply leave a comment and we’ll answer ASAP.

Should we drive Route 7 in Vermont from south to north or north to south?

Honestly, for this particular road trip on Vermont Route 7, it doesn’t really matter which direction you choose. If you are flying to the area and renting a car, you may want to base your decision on where you can get the cheapest, or easiest flight. 

If you fly into Albany International Airport (ALB) in New York State, you will be an hour from Bennington in Southern Vermont. We find lots of great flight deals in and out of Albany, which is the closest major airport from home. If you’re a fan of Southwest Airlines, like we are, then Albany Airport is a great choice.  

Burlington International Airport (BTV) also has good flight deals and car rentals too! Want to compare flights and car rental prices? Kayak is a great resource for finding the cheapest flights and car rentals to help you plan and budget for your trip.

When is the best time to travel on Route 7 in Vermont?

Route 7 is a well-maintained US highway, so technically, you can drive it during all four seasons. We recommend taking this Vermont road trip between May and October so you can take full advantage of farm stands, hiking, and swimming (okay, you may not want to swim in October, but you get the idea). 

The speed limit on Route 7 varies from 25 mph in towns and villages to 55 mph on certain stretches between towns, so no matter what time of year you plan to drive it, plan on taking your time!

When should we drive on Route 7 to see Vermont’s fall foliage?

That’s the million-dollar question! Instead of mountains along the Route 7 corridor, you’ll mostly get rolling hills and farmland. Because of the lower elevation, the trees tend to change a bit later than in the mountains. Fall foliage is reliably beautiful during mid-October. 

Will we have access to amenities while driving on Route 7?

Definitely! Route 7 connects a number of small towns, plus the relative metropolises of Rutland, Burlington, and St. Albans. In just about every town, you will find gas and groceries, and many towns also have numerous hotels, vacation rentals, and campgrounds. Yes, Route 7 in Vermont is mostly rural, but you’re never very far from civilization. 

What to Pack for Your Vermont Route 7 Road Trip

Wondering what to pack for your Route 7 road trip? I recommend keeping it casual. This part of Vermont includes lots of opportunities for outdoor exploration, and very few opportunities for nightlife unless you count chasing fireflies and relaxing under the stars. 

One exception is Burlington, which is a hip college town with live music happening somewhere every night of the week. One outfit for “going out” should be enough. Here are some more packing must-haves to help you make the most of your trip.

Activewear – Since you’ll be spending plenty of time outdoors, you’ll want to pack comfy clothes that are suitable for hiking. Opt for sturdy non-cotton pants ( like these ) and a breathable, moisture-wicking shirt. Merino wool shirts will keep you cool when it’s hot out and warm when it’s cold out, plus they don’t stink like polyester blends and they dry quickly.

Sturdy shoes – In summer, sandals that can double as water shoes are awesome for the lakeshore and rocky swimming holes. A pair of rugged hikers will be great for everything from walking in the woods to strolling through town.

Swimwear – Do not come to Vermont in the summer without a swimsuit! There are just so many great places to cool off! We use these quick-dry towels when traveling because the heavy cotton ones take too long to dry.

Jackets – Yes, the weather in Vermont is fickle, even in the summer. Between late May and August, you will be fine with a fleece and a rain jacket. For early spring and fall travel, add a down puffy jacket and a wool hat. These down jackets pack down really small and are perfect for travel.

Your Camera – Perhaps your phone doubles as your camera. Awesome! If your phone camera leaves something to be desired, consider bringing a separate camera to capture all the beautiful scenery. If you want a dedicated point-and-shoot camera that packs neatly into a backpack, check out the Canon PowerShot SX740 . Overall, this little camera takes better photos than the best smartphone with a powerful zoom and 4K video. I love traveling with mine!

Where to Next?

After traveling along Vermont’s eastern border and the shoreline of Lake Champlain, you can continue north into the Lake Champlain Islands, or head east into the Green Mountains. A Route 100 road trip would bring you south again, and we have another 5-day road trip itinerary for Route 100 if you want to extend your trip.  

If this is the end of your Vermont vacation, you can easily hop on Interstate 89 south toward Boston, or cross into New York and drive south on Interstate 87 to Albany International Airport. 

Planning a trip to Vermont? Be sure to check out our sister site, Vermont Explored , which covers all the best things to do in our home state!

Follow us on social media for more road trip ideas!

Tara is a freelance writer and travel blogger with a passion for outdoor adventures. She is the co-author of AMC’s Best Day Hikes in Vermont and currently blogs at Back Road Ramblers and Vermont Explored , where she shares travel tips, adventure destinations, and vacation ideas for the wanderer in everyone.

The Ultimate Vermont Road Trip: 11 Incredible Days!

By Author Disha Smith

Posted on Published: March 17, 2021  - Last updated: May 10, 2021

Categories Destination Tips , North America , Road Trips , Travel Tips , USA

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Vermont is a hidden gem of New England. While most people know it as a great fall destination or a wonderful stop on a New England road trip , the state rarely gets the attention that it deserves. Luckily, you’ll be able to experience more of the beauty of the Green Mountain State on this epic 11-day Vermont road trip.

While on this road trip, you’ll stop in state parks, small towns, and even a national forest! You can kayak on Lake Champlain, admire the fall colors in Stowe, visit the Ben & Jerry’s Factory in Waterbury, and try delicious maple syrup in Manchester.

In this post, I have come up with an amazing 11-day Vermont road trip itinerary. This plan will ensure that you see so much of the beauty that Vermont has to offer. That said, feel free to rework this itinerary to fit your preferences and style of travel.

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below.  See full disclosure here.

In This Post:

When Should I Go on a Vermont Road Trip?

Most people think that the only appropriate time to go on a Vermont road trip is in the fall when the lovely leaves are changing colors. And while I have to say that fall is definitely the best time for a Vermont road trip, it’s not the only time.

Summer is also an ideal time to go on a Vermont road trip. At that time of year, the state is filled with warm weather and lush greenery. Between the Fourth of July and Labor Day, Vermont actually becomes quite a popular place to visit.

After all, who wouldn’t want to swim in the crystal clear waters of Lake Champlain and hike through the beautiful natural landscapes of the many state parks?

Winter and spring in Vermont both have their ups and downs. While winter boasts picture-perfect snowcapped landscapes for snowshoeing and cross-country skiing, the freezing conditions can make driving difficult.

And although there are blooming flowers in the spring, locals refer to that time of year as “mud season,” because of all of the thawing snow mixing with the dirt.

Simply put, summer and fall are the two most amazing times for a Vermont road trip.

Basic Vermont Road Trip Packing List

What you should pack for your Vermont road trip greatly depends on the time of year that you’re doing to visit.

For example, if you’re visiting in the winter, you’ll want to load up on puffy jackets, warm sweaters, and fuzzy socks. And if you’re visiting in the summer, you’ll want to bring a swimsuit for a dip in Lake Champlain.

But regardless of when you visit, there are a few essentials that you’ll want to bring on your Vermont road trip.

Hiking Boots

Much of Vermont’s beauty comes from nature, and you’ll want to bring a solid pair of hiking boots to see as much of it as possible. When you visit destinations like Mt. Philo State Park and Smugglers Notch State Park, you’ll definitely be thankful that you decided to pack this functional pair of footwear.

Casual Clothing

There aren’t many spots where you’ll need to get dressed up while you’re in Vermont. Casual clothes, like jeans, flannels, and sweaters, are perfectly appropriate for the vast majority of places in the state.

The type of jacket you need to bring depends on when you plan to visit Vermont, but you’ll always want to bring a jacket of some sort. In the summer, a light rain jacket should do the job. But in the winter, you’ll want to bring the puffiest down jacket that you have!

RELATED: 12 Not so Obvious Items You Shouldn’t Travel Without

How to Start Your Vermont Road Trip

When starting your epic Vermont road trip, I recommend  flying into Burlington International Airport (BTV) . This airport is the largest airport in Vermont, making it the best place to start your adventure. Plus, you can easily rent a car here to start your road trip.

If you plan on doing this Vermont road trip during peak fall foliage season (October) and you plan on renting a car, make sure you reserve it well in advance. There may be a shortage because it’s such a popular time to visit the area. 

Or, if you’re looking for an even longer road trip, you can drive to Vermont from where you live. Don’t forget to check out my  road trip packing list  and make sure you have these 20 items before heading out on your adventure!

RELATED: Road Trip Packing List: 20 Things You Shouldn’t Travel Without

Where to Stay on Your Vermont Road Trip

Personally, one of the most time-consuming aspects of planning a road trip is deciding where I’m going to stay the night. I personally love Hotels.com . Their customer service is impeccable and they list some pretty great hotels, cabins, and more.

My favorite thing about them is that after you stay ten nights, you get a free night. I wrote a post highlighting the Hotels.com loyalty program (which is free to join) that you can read here . 

As you can see, these nights will add up on your Vermont road trip especially if you plan on extending your adventures in the area. 

Click here to book all of your Vermont road trip accommodations 

The Ultimate Vermont Road Trip

Whew — now that we have all the small details worked out, let’s plan your itinerary! As mentioned above, feel free to add more stops to your Vermont road trip. These are some of my favorite stops and I know you’ll enjoy them too.

To make your life easier, I included a short list of things to do in some of these destinations and a few of the best restaurants. So, all you need to do is basically pack your bags and hit the road!

Days 1-2: Burlington

We’re going to start this amazing Vermont road trip in the adorable town of Burlington. It’s touted as one of the most livable small cities in the USA. Even though it has a small-town vibe, it’s bustling with so many fun things to do!

During your two days in Burlington, you’ll easily be able to stay entertained. The most popular thing to do in Burlington is to enjoy Lake Champlain. Depending on the season, you can swim, boat, kayak, fish, or ice fish.

You can even visit one of the many Lake Champlain islands, including Grand Isle, North Hero Island, and Isle La Motte! There’s so much to do that you should definitely dedicate one full day to Lake Champlain.

As for your second day in Burlington, you have quite a few options. You can visit the Shelburne Museum , pick apples at Shelburne Orchards , bike along the Burlington Bike Path, or stop into one of the many wonderful breweries in town.

Things to Do in Burlington

• Shelburne Vineyard
• Church Street Marketplace
• Ben & Jerry’s (where the ice cream is manufactured)
• Brewery hopping — Vermont has the most breweries per capita in the United States. Some of the best breweries include Simple Roots Brewing, Weird Window Brewing, Burlington Beer Company, Zero Gravity Brewing, and Queen City Brewery. I highly recommend doing a beer tour while you’re here so you can get an insider’s look at the craft beer scene.  
• ECHO, Leahy Center for Lake Champlain
• The Fleming Museum of Art
• Ethan Allen Homestead
• Burlington City Arts Center
• Flynn Center for the Performing Arts

Where to Eat in Burlington

• Hen of the Wood
• Zabby & Elf’s Stone Soup
• Maya’s Kitchen and Bar
• Bistro de Margot
• For more restaurants, click here .

Day 3: Mt. Philo State Park

Your second stop on your Vermont road trip is Mt. Philo State Park . As the name implies, the highlight of this state park is the 968-foot Mt. Philo.

While there, you can enjoy everything nature has to offer. You can keep an eye out for deer and moose, delight in a lovely picnic while enjoying the views of the striking mountain, and even hike all the way to the top of Mt. Philo!  

Since Mt. Philo State Park is only 30 minutes outside of Burlington, you can continue to make Burlington your home base for the third day of your Vermont road trip. Or, if you like, you can camp overnight at Mt. Philo State Park.

Day 4: Button Bay State Park

Button Bay State Park is a lovely spot situated south of Burlington but still along the banks of Lake Champlain. With its gorgeous scenery, it’s the perfect place for day four of your Vermont road trip.

While in Button Bay State Park , you can enjoy just about any nature-based activity that you can dream of. You can hike, boat, fish, picnic, and look for wildlife. This state park even has its own swimming pool, complete with a small slide. You’ll easily be able to spend your entire day there!

Since Button Bay State Park is only 45 minutes outside of Burlington, you can continue to make Burlington your home base for the fourth day of your Vermont road trip. Or, if you like, you can camp overnight at Button Bay State Park.

Days 5-6: Stowe

On your drive from Button Bay State Park to Stowe, you’ll drive on the famous Route 100. This road is known as the most breathtaking place to see fall foliage in all of Vermont, so take your time on this scenic drive.  

When you reach the adorable town of Stowe, you may never want to leave. Stowe boasts that irresistible small-town vibe filled with cute shops, beautiful nature, and friendly people.

While in Stowe, you can take the gondola up to the top of Mount Mansfield (Vermont’s highest mountain), stop by the Stowe Foliage Art Festival, ski and snowboard at Stowe Mountain Resort, and even take to the skies during the Stoweflake Hot Air Balloon Festival.  

And while the town of Stowe is absolutely charming, you’ll want to dedicate at least one of your two days in Stowe to Smugglers Notch State Park. This beautiful state park is located just ten minutes outside of town!

While there, you can hike the Long Trail, test your ice climbing skills, or take a dip in the chilly waters of Bingham Falls.

Things to Do in Stowe

• Stowe Recreation Path
• Spruce Peak Performing Arts Center
• Stowe Cider
• Stowe Theatre Guild
• Cady Hill Forest
• Wiessner Woods
• West Branch Gallery and Sculpture Garden
• Sterling Falls Gorge

Where to Eat in Stowe

• Harrison’s Restaurant
• Butler’s Pantry
• Stowe Sandwich Company
• For more restaurants, click here . 

Days 7-8: Montpelier

This Vermont road trip allows you to see the amazing Route 100, not once, but twice . On your drive from Stowe to Montpelier, you’ll be able to experience this breathtaking route again!

With a population of just 8,000 people, Montpelier, Vermont holds the special title of being the smallest capital city in the U.S. But despite that fact, this little city is packed with things to do.

The main things to do in Montpelier can be grouped into two categories: nature and food . If you’d prefer the nature side of things, you can trek up Camel’s Hump Mountain, visit the Rock of Ages granite quarry , and do a little leaf-peeping in autumn .  

But if you prefer the food side of things, you can get a warm mug of apple cider at the Cold Hollow Cider Mill, grab a drink at one of the many local breweries, try a scoop or two of ice cream at the Ben & Jerry’s ice cream factory, and dive into Montpelier’s farm-to-table dining scene.  

Things to Do in Montpelier

• Vermont State House
• Hubbard Park
• Wine tasting at North Branch Vineyards
• Bear Pond Books
• Vermont Historical Society Museum
• The Coburn Covered Bridge

Where to Eat in Montpelier

• Sarducci’s
• Three Penny Taproom
• J Morgan’s Steakhouse
• Langdon Street Tavern

Day 9: Green Mountain National Forest

Day 9 of this Vermont road trip itinerary takes you to Green Mountain National Forest, one of the most stunning national forests in the U.S. – and that’s saying something, considering that there are 154 national forests in the country!

There are so many ways to spend your day at Green Mountain National Forest . You can hike a few of the gorgeous trails, such as Thundering Brook Falls Trail, Moss Glenn Falls, Trail, Texas Falls Trail, and even part of the Appalachian Trail. You can go for a swim at Warren Falls, Buttermilk Falls, and Hapgood Pond. In the winter, you can even ski, snowboard, and snowmobile.

And while you’re out on your adventures at Green Mountain National Forest, don’t forget to keep an eye out for some awesome wildlife, including moose, beavers, black bears, and white-tailed deer.

Days 10-11: Manchester

You made it! For your final stop on your Vermont road trip, you can explore the city of Manchester, Vermont (not to be confused with the nearby town of Manchester, New Hampshire).

There are loads of things to do in Manchester, so you can simply pick the ones that best suit your interests. You can drive to the top of the nearly 4,000-foot Mount Equinox.

If you’re into historic architecture, you can admire Hildene, which was once the home of Abraham Lincoln’s son.

If you’re a nature lover, you can hike to Lye Brook Falls, paddle down Batten Kill River, or picnic at Emerald Lake. Or you can take the road less traveled by paying a visit to the Robert Frost Stone House Museum.

But one of the best reasons to visit Manchester is for the maple syrup! Maple syrup is one of the most famous exports of Vermont, so you’ll definitely want to learn more about this sweet treat during your time in the state. There are many noteworthy maple syrup farms relatively close to Manchester, including Merck Forest & Farmland Center, Mitch’s Maples, and Green Mountain Sugar House.

While at these farms, you can learn about the maple syrup-making process, savor a few sweet treats, and even purchase some maple syrup to take home with you. If you’re extra lucky and you happen to be visiting in March or April, you’ll get to experience Vermont maple season! This is when the farms will be busy harvesting the sap and boiling it down into pure maple syrup.

Things to Do in Manchester

• Southern Vermont Arts Center
• The American Museum of Fly Fishing
• Manchester Depot
• Ye Old Tavern

Where to Eat in Manchester

• The Silver Fork
• Depot Street Burgers
• Ponce Bistro
• Sam’s Wood Fired Pizza Co.
• Zoey’s Deli

Where to End Your Vermont Road Trip

As they say, all good things must come to an end. I hope you had an amazing time on your Vermont road trip and that you’re returning home with some beautiful memories!

When you’re ready to head home, you can venture to one of Manchester’s nearby airports. The closest airport is the Rutland Southern Vermont Regional Airport (RUT), which is 30 minutes away. But this airport is only relevant if your destination is Boston because it only offers flights to Boston.

The closest major airport to Manchester is actually Albany International Airport (ALB) in New York. It takes about 1 hour and 30 minutes to reach this airport by car. This airport has flights to many main U.S. hubs, so you’ll easily be able to make your way back home.

There’s also the option to drive back to Burlington International Airport (BTV). While it takes two hours and 20 minutes to drive from Manchester to Burlington, there are a couple of perks to this option.

First, you’ll be able to buy a round trip airline ticket, which is sometimes cheaper than two one-way tickets. Second, you’ll be able to avoid the fee that usually comes with having different drop-off and pick-up locations for rental cars.

Vermont Road Trip Recap

Do you have any suggestions to add to this guide to the ultimate Vermont road trip? Let me know in the comments below!

Are you looking for more USA road trip inspiration? You’ll love these posts too!

New England Road Trip Itinerary: 10 Days Exploring the Northeastern US

The Perfect 10-Day Southwest USA Road Trip Itinerary

The Ultimate Florida Road Trip: 14 Epic Days!

Road Trip Packing List: 20 Items You Shouldn’t Travel Without

Disha Smith is the founder of Disha Discovers. She quit her job in 2017 to travel the world to explore new cultures and experience new adventures. She has since been to 95+ countries and counting and has lived in South Africa, Thailand, Croatia, and Australia. She has done all kinds of travel ranging from luxury to budget backpacking, and her mission is to inspire others to discover their own sense of adventure and to help them plan a life full of meaningful experiences through travel.

Sunday 30th of January 2022

Thank you so much for this post. I've been looking for a Vermont itinerary that lists things to do instead of just places to eat and shop. Really helpful! Also, I love hotels.com too. That rewards program is the best.

Disha Smith

Friday 11th of February 2022

You're very welcome, Paula! Thanks for reading. Hope you have a great trip to Vermont!

Ultimate Fall Foliage Road Trip in Vermont: A Complete Itinerary

Autumn is a second spring that turns all leaves into flowers”- Fall is definitely the time of the year when leaves speak to us, the story of existence as well as the beauty of letting things pass by. Fall leaves throw such a fantastic show before their demise. In this blog, we will cover awesome fall foliage road trip ideas in Vermont that may inspire your next adventure. Enjoy some stunning visuals of a Fall Foliage Road Trip in Vermont and get some help from our detailed itinerary to plan your Vermont road trip.

Vermont Road Trip Planner

Why fall is the best time to visit vermont, where to to stay in vermont, need a rental car in vermont, 3 day itinerary for a fall foliage road trip in vermont, stop 1: jamaica state park, stop 2: weston village, stop 3: plymouth, stop 4: woodstock village, stop 5: plainfield, stop 6: montpelier, stop 7: vermont state house.

• Stop 8: Ben & Jerry's Factory, Waterbury, Stowe

Tips to remember while traveling to Mount Mansfield

Stop 10: killington, pin this fall road trip in vermont for planning your trip.

New England on the east coast of the USA is one of the most gorgeous places to experience the ultimate beauty of Fall and the state of Vermont takes the crown . During the Autumn season here, you will have one of the best leaf-peeping experiences – whilst enjoying the natural Fall exhibition just during your drive, strolling in scenic state parks, hiking mountain ranges, or even exploring stunning waterfalls in this area. I came back with strong feelings for the state of Vermont and its people- it is by far my most favorite state in America. I will also go again, so let us say this was a beginning for me too.

Some of the top places to visit in Vermont in Fall include:

• Green Mountain National Forest
• White Mountain National Forest
• Scenic Route 100

The Fall foliage starts in mid-September and lasts until mid-October. I visited at the beginning of October when the leaves are more reddish however if you’re looking for yellow colors, visiting earlier is advised. Personally, I would recommend aiming for “Peak Foliage” in mid-October and the USA long weekend of October 12th for Columbus day is perfect for this Fall Road Trip.

Vermont is more like a European Travel experience when it comes to the stay. There are many inns and B&Bs run by locals which I would recommend as your first choice to experience the local life. I stayed in a lovely Airbnb which was very similar to a Scottish B&B and I would rate my stay here as one of the best Airbnb stays ever.

If you are visiting internationally flying into New York or Vermont, you could go for a rental car option. Remember that you drive on the right side of the road in the USA. Your international driving license is valid if you feel comfortable driving. The rules are pretty easy with wide roads and clear junctions combined with the fact that most of the cars in the USA are automatic.

*Disclaimer: This post contains affiliate links. If you click on them and make a purchase, I receive a small commission. There is no additional cost to you. I would appreciate the support.

We embarked on a Vermont Fall road trip as part of a Week East Coast Road trip traveling from Florida to Boston. This Vermont road trip itinerary starts from Albany and made our up North with stops at villages and parks in the Green Mountain National Forest until arriving at Montpelier , the capital city of Vermont. In the following days, we also covered the Vermont scenic 100 route and two mountain ranges, Mount Mansfield and Killington. Below is the route we followed color-coded per day for this amazing fall foliage road trip in Vermont. Let us enjoy the fall visual show of Vermont together.

READ: Best Road Trips in USA for your American Road Trip Bucket List

Day 1: Green Mountain National Forest

Our first stop in Vermont was the Jamaica State Park which is located in a small picturesque village Jamaica in the south of Vermont. The state park needs a pass to enter and it is best to check the activities before you go. We only strolled around the village. 

The short walk from the village to the park is stunning with amazing views of colorful houses embedded into nature along the West River and an amazing bridge called the Wardsboro bridge forming a great frame.

There is a hike from here to the Ball Mountain Dam via Hamilton Falls which we missed as our itinerary was tight, I would advise planning to spend a long time here. From here we headed upwards to the village of Weston. On the way, you will get this stunning view which is the same as my feature image. Here is the exact stop: 60-52 River Road, Jamaica, VT 05343.

Weston felt was like walking through a European town with the houses, roads, and shops here reminding me of Austria/Switzerland. Adding to the Autumn charm, the village houses were fully decorated with pumpkins all ready for Halloween. I really loved the orange theme in this postcard-perfect Green Mountain Town village in autumn.

There are some really cute little shops here selling local crafts and produces. I had heard that this town is perfect to celebrate Christmas in, and the Christmas shop here really had strong European vibes so you can note this village if you’re planning a European-style getaway in the USA.

Another attraction is here the Old Mill Museum , which has a mountainous backdrop and a stunning waterfall. We did not go inside the museum as it was closed the day we visited however the view from the outside museum was breathtaking enough for us. Someone from the village had even left a pumpkin beneath the trees, how cute!

The route to Woodstock via Plymouth was one of the best scenic routes during the trip. We didn’t stop in the town itself but we just stopped along the way to admire the views.

The view of mountains and reflections in the lake is simply splendid. This route is just stunning throughout so much so it was confusing which pictures to take and which pose would be best. In the end, I can see we ended up taking fewer pictures and spent more time just enjoying the view. 

We arrived in Woodstock village around sunset, of course, this is what happens if you take a scenic route and keep stopping. Woodstock village is very famous in New England and is on the top list of scenic towns with amazing houses and post-card views around. Though we missed exploring the village properly, we could experience the local shop here which was so thrilling with lots of diverse farm productions. I almost wanted to buy everything and the bakery here was calling to us loudly.

These pumpkins and Squashes are just a small part of what they produce. Aren’t they so diverse? I have never seen these shapes and colors before, I spent a lot of my time just staring at pumpkins and I wished I could have brought them home with me. 

After strolling here, we headed towards Montpellier where our Airbnb was booked for the night.  I definitely need to go back to Woodstock as I could not explore it properly. We arrived late in Montpellier, found a local Thai restaurant to eat at, and headed to the Airbnb to crash.

Day 2: Scenic Route 100

Waking up in Plainfield, Montpellier in our Farm Stay Airbnb is still one of my most favorite stay experiences. This house is located in a private estate with a lake and the morning view was breathtaking. Our host was such a lovely lady who had everything sorted for us like a typical B&B in Europe. They also had an Apple tree with such low-hanging apples that I tried to act eating one while standing on the ground.

The Airbnb farm house has a vintage style and is decorated very well. The prayer flags caught my attention and I added them to my list of home decorations straight away. I wish we had more time here, I will definitely go back and stay exactly here again if it is still available.

The Airbnb was in a hilly area far away from the city. We headed towards Montpellier city first.

We stopped at Montepellier and went via Cliff Street towards Hubbard Tower to get a top view of the city. There were a lot of hikers around here and would recommend not missing this view if you visit. This town qualifies to be the most scenic Fall Town view in my mind, just like I have Tromso for the best winter view. The capital city of Vermont and the vibes here caught my attention, there is something so positive about the people and region here.

The State House of Vermont is located in its capital town, Montpelier. Stopping by this cute statehouse was a heartwarming experience as it stood gorgeous and constantly reminded me of the Glory of this State and its People. It was just stunning with its golden dome and fall backdrop. 

We drove towards Stowe taking the scenic route 100 . This drive was just epic and was sad I could only do a part of it and hope to revisit and finish the full route.

Stop 8: Ben & Jerry’s Factory, Waterbury, Stowe

We arrived at the original Ben and Jerry’s factory which is the Mekkah for Ice-cream lovers. The vibe here is too cheerful, both adults and kids queued up to get their hands on their favorite flavor. 

Here you can taste all their new flavors and pay a visit to the ice-cream graveyard where there is a gravestone for every flavor that didn’t succeed in the market.

Stop 9: Mount Mansfield

One of the highlights of my trip was the drive and hike up to Mount Mansfield, the highest mountain point in Vermont. This literally felt like being in a Hollywood movie even looking at cars coming down from that steep hill while we queued to drive up. 

Climb up and you are in the middle of a FALL HEAVEN literally. It is all Yellow, the Coldplay song was singing in my head throughout the drive here. This mountain is a not-to-miss and the best for leaf-peeping and complete with a cute little chapel.

The drive can be tricky here and we saw a couple who had got stuck with their car tire wedged in a ditch. There are multiple trails you can do here and it is best to plan time if you wish to hike.

We just did a short section of the Sunset Ridge Trail as we did not have much time left of the day. The view from here is amazing.

A list and map of trails can be found here.

Day 3: Killington

At this point, one of our friends had to leave so we had a short break in the trip before the rest of us continued to visit Killington the next day which is another mountain range famous for skiing. Look at the view- amazing isn’t it?

The Killington Mountain Lodge is very popular among families and was packed during our long weekend visit. It is perfect for a Fall Foliage road trip in Vermont, particularly for a weekend getaway and they have amazing rooms to stay in here. 

Click here to find some amazing accommodation options in Killington

Final thoughts on the Fall Road Trip in Vermont

Fall Road trips in Vermont are the best for leaf peepers, nature lovers and foodies. What attracted me the most during my Vermont visit, apart from the leaf-peeping experience, and picturesque villages are the really nice people and their commitment to using local products that even McDonald’s does not exist there. Vermont is known for its natural landscape, and its capital town Montpelier is amongst the least populated cities of the USA. It definitely is an Autumn Wonderland!

Jumana is a travel writer and technologist living in the United Kingdom, born and brought up in India. While she is busy with her full time job as a computer technologist, she is an active explorer during her spare time. She has been exploring states of India since she was 15 and then around the world since she moved to the west in her 20s. Her favourite travel style is “On the Road” and she has perfected the art of road trip planning, covering multiple famous and undiscovered routes around Europe, UK and USA. She is on a mission to road trip the planet and learn more about the cultures around the world.

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73 comments

Vermont is beautiful all around the year and Fall is the best!

Thanks Deep. No doubt Vermont rules for Fall

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Vermont Road Trip – 3 Day Travel Itinerary (2024 Guide)

Vermont is such a special state. It’s stunningly beautiful, even when the leaves aren’t changing. It’s small enough that you can easily drive around the entire state on a road trip. And its well known for a whole handful of things. Here are our favorite things to do in Vermont and a 3 day road trip itinerary to see the best of Vermont in just a weekend.

What To Do in Vermont – 10 Must Do Activities

• Take a photo of a covered bridge. Bonus points if it’s red.
• Visit a quaint little town. The quintessential New England town has a certain look, and Vermont is full of them: red barns, a white church, houses dotting the hillside, the colorful fall leaves.
• Tour a maple sugar farm. Learn about sugaring and taste the sweet results.
• Eat all the maple things – maple syrup, maple candy, maple ice cream (also known as a creemee), maple cocktails, maple taffy (a favorite!), maple popcorn, maple cream, and maple lattes. You’ll also find maple added to hot sauce, salad dressing, BBQ sauce, chocolates, flavored nuts, and many other food items. And if you want the FULL maple experience, you’ll want to plan your trip around the Vermont Maple Festival held each April.
• Go leaf peeping in the fall.
• Stop at Ben & Jerry’s. Tour the factory, get a treat from the scoop shop, and visit the flavor graveyard. Our favorite photo spot: the cow-painted Airstream.
• Drive Route 100. Spend a day or two on the backroads of Vermont, stopping at waterfalls, small shops, and casual cafes.
• Visit the Trapp Family Lodge, founded by the von Trapp family of Sound of Music fame.
• Enjoy cheddar cheese, perhaps alongside a visit to Cabot Farmer’s Store or Shelburne Farms.
• Drive Smuggler’s Notch, a scenic road stretching from Stowe to Jeffersonville.

Where To Stay On Your Vermont Road Trip

This Vermont road trip itinerary starts in Stowe, goes down to Grafton, and returns through Montpelier and Waterbury. I’d recommend a night at the Green Mountain Inn or Trapp Family Lodge in Stowe, then the Grafton Inn, and then finally Hollister Hill Farm Bed and Breakfast.

If you’d like to camp as part of your Vermont road trip, you’ll probably want to keep your RV parked near Stowe. Gold Brook Campground or Mountain View Campground are two close by options.

Where We Stayed:

Harvest Hosts has some amazing options here! We stayed at two maple sugar farms and had creemees in our own backyard! ( Find out more about Harvest Hosts and how you can have amazing experiences while camping at unique places.)

Best Things To Do in Vermont with Kids

Before we get to the specific itinerary, I wanted to mention a couple of stops that our kids really enjoyed. If scenic drives, shopping, and covered bridges don’t appeal to your kids, here are some things to highlight during your trip to keep them engaged.

Martin Covered Bridge – This covered bridge has been turned into a little park, so there’s space for kids to run and stretch their legs. If your kids aren’t interested in the history of covered bridges, this is a great stop to get the whole family involved.

Maple Sugar Farms – Tasting maple syrup, choosing a candy from the 25 cent jar by the register, enjoying a maple creemee… it’s an all-around win! We also really enjoyed the kids’ educational video offered at Bragg Farm Sugar House. The farm also has goats, ponies, and a small playground, so it’s a must-do spot for families.

Ben & Jerry’s – Obviously kids are on board anytime there’s ice cream involved. In addition, the Flavor Graveyard is fun to explore and they have a playground too.

Cold Hollow Cider Mill – A cider tasting, lawn games, and cool old farm equipment are all fascinating to my boys.

Queechee Gorge – We had to skip this stop for time, but I know our boys would have loved climbing out on the rocks.

Kids Books About Vermont & Maple Sugar Farms

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Sugar on Snow by Nan Parson Rossiter Taffy Time by Jennifer Lloyd Sugarbush Spring by Marsha Wilson Chall Winter Barn by Dorothy Ripley Maple Syrup Season by Ann Purmell How to Tap a Maple by Stephanie Mulligan Almost Time by Gary D. Schmidt Maple Syrup from the Sugarhouse by Laurie Lazzaro Knowlton The Sweetest Season by Elissa Kerr Grandpa Alan’s Sugar Shack by Alan Page Sleep Tight Farm by Eugenie Doyle

Vermont Road Trip Tips

Don’t miss out on the specialty maple items. Nearly everywhere we went sold maple syrup and maple candy. Maple ice cream, taffy, and popcorn were the next easiest to find. But I found myself wishing that I’d gotten a jar of maple cream (and even that I’d bought a little more taffy), because some items are less common than others. Best rule of thumb: if you see something you’d like, buy it here unless it’s maple syrup or maple candy. Then make sure you have one good maple stop at the end of your trip to make sure you have everything you were hoping to take home.

If you’re traveling in the fall when the leaves are changing, pack your patience. There’s a reason Vermont is famous for this time of year and everyone wants to enjoy the fall foliage! Slow down a bit and savor the scenery in front of you. It’s ok if you don’t get to everything on your list. Your leaf peeping trip is still going to be amazing!

Know how tall your vehicle is. The lowest bridge clearance we saw on our route was 10 feet, but we didn’t get a chance to see all of the ones I’ve shared here. Some covered bridges are pedestrian only for preservation, but it’s a good idea to know just in case.

Pack for it to be both colder and hotter than you think. We were surprised at how much the temperature varied throughout the day and during the length of our trip. We arrived during a heat wave, and I was wishing for my sweatshirt when it was time to go home!

3 Day Vermont Itinerary

Here’s a 3 day itinerary for spending a long weekend in Vermont, starting in the beautiful town of Stowe. Over the course of 3 days, you’ll hit 3 waterfalls, 12 covered bridges, and countless amazing Vermont gift shops!

Day 1 – Stowe

About 1 hour of driving around Stowe

Moss Glen Falls

Start the day with a short hike at Moss Glen Falls. The parking area only holds about a dozen cars, so early in the day is always a good idea.

Stowe Village

Stop at Black Cap Coffee for a maple latte and pastry and then wander Stowe Village in the late morning. Our top 2 stops would be Café on Main for lunch and a maple creemee and Laughing Moon Chocolates for maple flavored truffles (or just about any other chocolate treat you could dream up). You won’t want to miss the Stowe mural on the side of the building at Laughing Moon Chocolates.

Some other stops you might enjoy: Stowe Community Church, The Country Store on Main, Stowe Sweet’s ice cream shop, Shaw’s General Store, Stowe Mercantile, Bear Pond Books Store, Vermont Ski & Snowboarding Museum, and Once Upon a Time Toys.

You might also enjoy a walk or bike ride on the Stowe Recreation Path, which starts in a parking lot behind the church and follows the West Branch of Little River for a little over 5 miles. Fun fact, this pathway is open for use in the winter too, so strap on your snowshoes or cross country skis! Here’s a helpful map .

Stowe Village Overlook

When you’re ready to do a little exploring, hop in your car and stop at the Salon Salon parking lot for a beautiful overlook of Stowe Community Church. (Turn right and park in the lot down the hill to save parking space for salon customers.) This is a popular overlook for that iconic fall foliage shot.

Covered Bridges

In addition to the pedestrian covered bridge right in Stowe Village, Brookdale Bridge and Gold Brook Covered Bridge (also called Emily’s Bridge) are just a short drive away.

Dinner at Trapp Family Lodge

Visit Trapp Family Lodge for dinner and a walk around the grounds and enjoy the beautiful mountain views. Make reservations for their dining room, have drinks on the patio, or visit the Von Trapp Beirhall to experience ‘a little of Austria, a lot of Vermont.’ I especially enjoyed the framed illustrations from The Trapp Family Book by Hans Wilhelm along the hallway to the Lodge’s restaurant.

Hike Sunset Rock Trail

Sunset Rock Trail is a short but steep hike to an overlook of Main Street. If you continue past the overlook point, you’ll also find Glacial Kettle Hole, a whirlpool-eroded rock formation. Past that is the Upper Overlook view of Mount Mansfield.

Accommodations: Stay overnight at Trapp Family Lodge or in the center of Stowe at Green Mountain Inn.

Day 2 – Route 100

4.5 hours of driving from Stowe to Wilmington and then back up to Grafton – leave yourself lots of time for stops!

Today you’ll drive 150 miles from Stowe to Wilmington on Route 100. This should take about 3.5 hours without stops. I’ve listed some route highlights below if you’d like to plan out what interests you most. If you prefer to just hop in and drive, keep in mind that Killington, VT is about the halfway point of the drive, and you’ll need to save about an hour at the end of the day to drive up to Grafton.

The 3 foods Vermont is best known for are maple syrup, cheddar cheese, and Ben & Jerry’s ice cream. We’re going to taste them all today. Whether you choose to stop at all the gift shops, do a string of hikes, soak in all the history, or make it a food tour, driving down Route 100 is sure to be a memorable day.

If you’d like a guided tour, consider downloading the GyPSy Guide to Route 100 .

Fun Route 100 Stops from North to South:

Stowe Maple Products – Purchase maple gifts like caramels, maple cream, and brittle.

Vermont Artisan Coffee and Tea – Stop for a coffee or tea and take a tour of the roastery.

Cold Hollow Cider Mill – Take a peek at the cider making process and try a sample in the back of the shop. You’ll find lots of great gift options here with many different kinds of Vermont-made food items.

Lake Champlain Chocolates and Cabot Farmer’s Store – These shops are side by side and would make a yummy pit stop either savory or sweet.

Ben & Jerry’s – If your day isn’t too full of sugary treats already, stop off at Ben & Jerry’s for their factory tour, a cone from their scoop shop, and a walk around the infamous Flavor Graveyard. My favorite gravestone was Sugar Plum and my boys loved Fossil Fuel.

Hartshorn’s Organic Farm Stand & Maple Sugar House – Farm tours, cow train rides, and brick oven pizza make this a unique farm stand stop.

Canteen Creemee Company – Fried chicken, burgers, and over-the-top creemee creations. What a fun stop on your Route 100 road trip!

Mad River Taste Place – This gourmet grocery store is a great stop for Vermont cheese and other food gifts.

The Lareau Park – A popular swimming spot.

Warren Falls – Limited parking, but beautiful stepped waterfalls and a great swimming hole.

Moss Glen Falls – There are two waterfalls in Vermont with the same name, and to make things even more confusing they’re both located on Route 100. Moss Glen Falls in Stowe was mentioned above. This is Moss Glen Falls in Granville and it is stunning!

Original General Store – A great stop for gifts or for a yummy lunch.

Amherst Lake and Echo Lake – Enjoy looking out the window as you drive right alongside these two beautiful lakes.

Green Mountain Sugar House – Pick up maple sugar coated nuts or brittle or one of their many gift packages.

The Old Mill Museum in Weston – A beautiful scenic spot with a red mill along the water, especially with fall foliage.

The Vermont Country Store Weston – Vermont gifts, old fashioned apothecary section, and a selection of Christmas decor!

Covered Bridge in Jamaica – Turn off Route 100 onto Island Lane to see this bridge. The big open windows make it a great spot for photos or for river viewing.

Sticky Fingers Bakery – Cakes, freshly baked bread, and their signature cinnamon rolls.

From Wilmington, drive East, stopping at Vermont Distillers and Hogback Mountain Country Store and enjoy the overlook here. Visit The Robb Family Farm Sugar House to learn about sugaring and taste their maple syrup. Then you’ll want to see the Creamery Covered Bridge and the Dummerston Covered Bridge on your way to Grafton.

Accommodations: Stop for the night at the Grafton Inn. If you didn’t stop for dinner along the way, 1801 Tavern at The Grafton Inn is a perfect choice to round out the day.

Day 3 – Drive and Montpelier/Waterbury

3 hours of driving from Grafton to Waterbury

Three More Covered Bridges

Today we’ll drive north to Waterbury, stopping first to see Bartonsville Covered Bridge and Worrall Covered Bridge on our way to the highway. Then we’ll stop at The Vermont Country Store Rockingham. Your trunk is probably full of gourmet foods already, but if you missed the Vermont Country Store in Weston yesterday, you might enjoy browsing here. Either way, be sure to stop and see the Kissing Bridge and the old Grist Mill.

Queechee Gorge

Several trail options are available here. Walk the trail to the dam or climb down into the gorge. And don’t miss the view of the gorge from the bridge! The visitor center is located in a separate parking lot.

If you want more than the snack bar for lunch, check out Pizza Chef of Queechee or get breakfast-all-day at The Skinny Pancake.

Taftsville Covered Bridge

Before returning to the highway, drive by Taftsville Covered Bridge. Note that this bridge has a 10 foot clearance (only if you can drive through the 10 foot clearance, and there isn’t really any space to stop and take a photo, so skip this one completely if your vehicle doesn’t fit through.

Maple Sugar Farms in Montpelier

If time allows, visit both Morse Farm Maple Sugarworks and Bragg Farm Sugar House. They each have a video you can watch about the sugaring process, a self guided tour of the sugarhouse, and a free maple syrup tasting. They also both sell maple creemees. We liked the presentation at Morse Farm the best, but Bragg Farm’s creemee was tastier, so it’s hard to choose between them. Both shops have a variety of other wonderful gift items in addition to the classic maple selection. We also highly recommend the maple ‘kisses’ (taffy).

Two More Covered Bridges

Before heading to the bed and breakfast, drive through the Covered Covered Bridge on your way to the Martin Covered Bridge. This stop was a favorite of ours, because it’s been turned into a little park with trails and space to picnic.

Accommodations: Stay overnight at Hollister Hill Farm Bed and Breakfast.

Extend the Trip

4 day vermont itinerary.

Add a day (or two) to your Vermont itinerary, by exploring Shelburne & Burlington. Spending a day at Shelburne Farms and wandering downtown Burlington would be at the top of my list.

If you want to widen your trip outside Northern Vermont, Manchester, Grafton, and Woodstock are all very scenic towns worth a visit.

Or if a dozen covered bridges isn’t enough for you, you could go all in and do an even bigger driving loop! You can find a map of Vermont’s many covered bridges here .

See more of our New England series: 2 Day New Hampshire Road Trip Itinerary 4 Day Coastal Maine Road Trip Itinerary Ultimate Guide to Acadia National Park 4 Day 3 State New England Road Trip Itinerary

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10 Scenic Stops Along Your Vermont Road Trip Itinerary

A pleasant loop from Stowe to Wilmington, Montpelier, and back, covering 367.7 miles or 7 hours and 29 minutes of total drive time.

• Diverse Landscapes and Outdoor Adventure: Vermont's road trip offers a range of landscapes, from vibrant woodlands to lake shores, providing ample opportunities for outdoor activities like hiking, biking, and skiing.
• Historic Charm and Cultural Richness: The towns along the route, such as Ludlow and Bennington, showcase rich history through attractions like covered bridges and museums, while places like Brattleboro offer vibrant arts and literary scenes.
• Seasonal Appeal and Scenic Beauty: Each town, including Manchester and Wilmington, boasts unique charm in different seasons, emphasizing Vermont's scenic beauty with trails, parks, covered bridges, and mountain views.

Road trips are one of the most enjoyable and adventurous ways to explore a certain region or country, especially when there is no time or budget constraint. Case in point: this itinerary from Jacksonville to Miami boasts several scenic towns and cities along the way. Another compelling journey to consider is this exploration of Far West Texas from El Paso to Big Bend National Park .

It goes without saying that the nation is chock-full of such invigorating and picturesque opportunities, and Vermont is no less fascinating and worthy of in-depth exploration.

Here is a proposed loop that will take road trippers along a wide array of charming stops within the Green Mountain State, from Stowe to Wilmington to Montpelier and back , covering roughly 367.7 miles or 7 hours and 29 minutes of total drive time in the span of 10 days.

Vermont To Quebec: Everything Confirmed So Far About This New Amtrak Route

10 stowe to shelburne, distance traveled: 39.8 miles if a straight drive.

From sipping craft beer to hiking through vibrant woodlands , Stowe, a charming town in northern Vermont , always provides memorable experiences in all seasons. Nestled at the foot of Mount Mansfield, the state’s highest peak, it is known for its friendliness, ski slopes, and picturesque trails, a perfect starting point along this long road trip.

• Places To Stay: Best Western Plus Waterbury-Stowe (from $166); Holiday Inn Express South Burlington (from $126)
• Top Attractions: Waterbury Center State Park (10 am to sunset; $5/adult/day), Bolton Potholes waterfalls; Historic Round Church in Richmond (10 am to 4 pm); Winooski Footbridge
• Trails: Warren and Ruth Beeken Rivershore Preserve (easy; 7 miles; 2 hours 11 minutes); Duxbury Window Trail (challenging; 3.1 miles; 2 hours 13 minutes)

9 Shelburne To Killington

Distance traveled: 70.2 miles if a straight drive.

Shelburne is a charming town in Chittenden County along the shores of Lake Champlain. It makes for a worthy stop with its hearty restaurants, folk museum, vineyards, farms, historic district, and antique shops, not to mention the astounding scenery in its vicinity.

• Places To Stay: Inn at Charlotte (from $189); Greenbrier Inn (from $169)
• Top Attractions: Mount Philo State Park (free; $3/adult from Memorial Day to Columbus Day; 8 am to 5 pm); Rokeby Museum and historic farm in Ferrisburgh (Mid-May to mid-October; 10 am to 5 pm; $10/adult); Halpin Covered Bridge and gorge view; Lake Dunmore ; Green Mountain National Forest (free; seasonal hours)

Lake Dunmore is ideal for boating.

8 Killington To Ludlow

Distance traveled: 21.8 miles if a straight drive.

Located in the Green Mountains of central Vermont, Killington offers top-rated hotels to experience the striking beauty of autumn , biking and golfing opportunities, popular ski resorts, and a vast choice of stunning trails in forests and parks. It is an ideal stop to partake in relaxing and energizing outdoor activities.

• Places To Stay: Killington Bear Mountain Lodge (from $180); Hawk Inn and Mountain Resort; Main + Mountain Bar & Motel (from $146); Camp Plymouth State Park (cottage from $97/6 people/night)
• Top Attractions: Coolidge State Forest (10 am to sunset; $5/day)
• Trail: Buttermilk Falls Trail (easy; 0.5 miles; 12 minutes)

10 Cozy Towns To Retire To In Vermont

7 ludlow to manchester, distance traveled: 31.9 miles if a straight drive.

A former mill town, Ludlow is a popular ski destination in Windsor County that can be enjoyed every season as a charming and thrilling stop along a Vermont road trip. Its main attraction is the high-end Okemo Mountain Resort , which not only offers panoramic views, but also numerous outdoor activities like golfing, hiking, ice skating, and snowboarding.

• Places To Stay: Hampton Inn and Suites Manchester (from $152); Kimpton Taconic Hotel (from $180)
• Top Attractions: American Museum of Fly Fishing (Thursday to Saturday; 10 am to 4 pm; $5/adult); Historic Quarter; Hapgood Pond Recreation Area (Memorial Day to Columbus Day; 6 am to 10 pm; $5/day)
• Trail: Prospect Rock Trail (moderate; 3.1 miles; 2 hours 58 minutes)

6 Manchester To Bennington

Distance traveled: 26 miles if a straight drive.

Located in Bennington County, Manchester is a unique destination and a memorable stop with stunning mountain landscapes, lush river views, and a quaint, historic downtown . Its main attraction is the opulent Hildene Estate and its colorful gardens, the family home of Robert Lincoln, President Lincoln’s eldest son.

• Places To Stay: The Inn at Manchester (from $185); Hampton Inn Bennington (from $156)
• Top Attractions: Hildene (Thursday to Monday; 10 am to 4:30 pm; $23/adult); Chiselville Covered Bridge; Peter Matteson Historical Tavern; Manchester Riverwalk
• Trails: Lye Brook Falls Trail (moderate; 4.5 miles; 2 hours 15 minutes); White Rocks Cliffs Trail (moderate; 3.2 miles; about 3 hours)

Manchester is particularly picturesque in spring and fall.

5 Bennington To Wilmington

Distance traveled: 20.5 miles if a straight drive.

Considered Vermont’s first town, and therefore a must-visit on a road trip thanks to its historic and natural sites, Bennington is known for the titular battle that took place during the Revolutionary War. The locals' main public focal point is Willow Park , which includes a golf course and a playground and hosts sports and social events.

• Places To Stay: The Autumn Inn Bennington (from $85); Viking Motel Wilmington (from $96)
• Top Attractions: Molly Stark State Park (10 am to sunset; $5/day); Stamford Stream; Big Pond Lake ; Woodford State Park (10 am to sunset; $5/adult); Medburyville Bridge; Harriman Reservoir swimming lake ; Bennington Battle Monument; Woodford State Park (10 am to sunset; $5/day)

These Are The 10 Prettiest Vermont Towns To Visit For Christmas

4 wilmington to brattleboro, distance traveled: 19.6 miles if a straight drive.

Not to be confused with its namesake, Delaware’s largest city, known for its gardens and breweries , Wilmington is a tight-knit and artisan-oriented community in Windham County, at the southern end of the Green Mountains. It is surrounded by hiking trails, lakes, mountains, and forests, making it a picturesque and welcoming stop on that postcard-perfect Vermont road trip.

• Places To Stay: Colonel Williams Inn in Marlboro (from $175); Colonial Motel & Spa in Brattleboro (from $86)
• Top Attractions: Wilmington Historic District; Green Mountain Beach; Hogback Mountain Conservation (9 am to 5 pm; free); Creamery Covered Bridge

3 Brattleboro To Hartford

Distance traveled: 65.1 miles if a straight drive.

Affectionately shortened to Bratt, Brattleboro is another leafy town in Windham County , but it also boasts an active art, literary, and food scene. Its cozy restaurants offer hearty farm-to-table dishes, and there are fun community contests and events all year long. It surely deserves to be explored on that 10-day excursion.

• Places To Stay: Best Western Springfield (from $152); Hotel Coolidge (from $92)
• Top Attractions: Bellows Falls Village Forest; Mount Ascutney State Park (10 am to sunset; $5/day); Windsor Town Forest; Spodie Rock

Mount Ascutney State Park offers cabins and cottages for $60/night .

2 Hartford To Montpelier

Distance traveled: 51.5 miles if a straight drive.

Windsor County’s Hartford may be much smaller than the capital of Connecticut and its award-winning attractions , but it offers a multitude of public parks and athletic fields, as well as entertaining annual events that include the Valentine’s Day Dance, the Summer Concert Series, and the New Year’s Eve Skate.

• Places To Stay: Comfort Inn & Suites Montpelier-Berlin (from $185/night); Margaret Holland Inn (from $149/night)
• Top Attractions: Vermont Vietnam Memorial; Berlin Pond
• Trails: White River Ledges Trail (moderate; 1.6 miles; 54 minutes); Quechee Gorge Dewey Pond Trail (easy; 2.8 miles; 1 hour 1 minute)

10 Incredible Caves Worth Seeking Out In Vermont

1 montpelier to stowe, distance traveled: 21.7 miles if a straight drive.

As the capital of Vermont, Montpelier is a fitting ultimate stop on that scenic journey from and to Stowe. Since it is the least populated state capital in the nation, it has retained its small-community vibe despite offering both indoor and outdoor activities and attractions, from museums to historic buildings, art galleries, concert venues, parks, craft beer bars, and organic eateries.

• Places To Stay: Mountain Meadow View B&B ($140)
• Top Attractions: Hubbard Park and its historic tower (7 am to 9 pm); Kenneth Ward Park (6 am to 8:30 pm; free); Waterbury Village Historic District; Gold Brooke Covered Bridge; Pinnacle Meadow ; Vermont State House (Monday to Friday; 8 am to 4 pm; free)
• Trail: Winooski West Path (2.6 miles; 47 minutes)

12 Of The Very Best Vermont Road Trips You Can Take

Kristin Grimes

Kristin Grimes lives in Vermont, is a freelance writer and busy MOM (Manager of Madness) and WIFE (Washing, Ironing, Feeding, Etc.)

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Whenever you start to feel a little stir-crazy here in Vermont, it’s time to hit the road! Many of us have resolved to do, see and experience more of our own backyards, and what better way to do that than taking some of the most unforgettable Vermont road trips! The Green Mountain State has so many places to explore, so we’ve gathered up some of our favorite road trips featured over the years. Gas up the tank and get on your way!

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Which one of these Vermont road trips would you like to do? Let us know in the comments below!

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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Vermont road trips.

What are the most unique towns in Vermont?

Stowe is a one-of-a-kind town that manages to fit a busy tourist destination into a tiny village without ever feeling too crowded. Come in the springtime and you'll have the place practically to yourself, which makes it easy to get to know local life. Visit Chester to see Stone Village Historic District and Chester Village Historic District. Many of these historic homes were made with local granite! Woodstock may not be as famous as the other Woodstock, but it's a charming town with a vibrant community that's sure to capture your heart.

What's the most beautiful hike in Vermont?

The hike to Bingham Fall's in Stowe is one worth taking! It's only about twenty minutes to the falls, but the beautiful mountain landscape is sure to impress. The hike to Falls of Lana in Salisbury will take you up from the shores of Lake Dunmore into the foothills of Moosalamoo National Recreation Area, making for a scenic trek in any season.

Does Vermont have any natural wonders?

The Green Mountain State is full of beauty and remarkable natural wonders . Some of our favorites include Lake Dunmore, at the base of Mt. Moosalamoo. It's the gateway to Green Mountain National Forest! Another one of our favorite lakes, Lake Ninevah, is in Mt. Holly, along the Eastern Gateway region. Quechee Gorge is a must-visit spot that many locals refer to as Vermont's Grand Canyon thanks to the enormous gorge and cascade waterfall. Smuggler's Notch is home to a few natural wonders, too - there are a handful of caves and the beautiful Bingham Falls.

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Featured Addresses

10-Day New England Road Trip Itinerary

• New England offers a variety of destinations for a memorable road trip, including Boston, Cape Cod, Providence, and more.
• Boston, Massachusetts, is one of the best New England road trip stops, known for its historical landmarks and museums, although it can be pricey and congested.
• Bar Harbor, Maine, is a must-visit when road-tripping New England in 10 days; it's perfect for nature enthusiasts, as it's home to Acadia National Park, while Portland, Maine, is a charming waterfront city with a blend of history and innovation.

The moniker of New England brings a great deal of curiosity to those looking for a new area of the world to explore. As a collection of states spanning Maine, Connecticut, Massachusetts, Vermont, Rhode Island, and New Hampshire, ample opportunities exist to take in all the area has to offer through an old-fashioned road trip.

Deciding on a route that will accommodate the top destinations New England has to offer is half the battle. The 10-day road trip below combines heritage, entertainment, and cultural opportunities to ensure a well-rounded and memorable vacation. All that's left to do is to buckle up and enjoy the adventure yet to come!

Related: These Are The 14 Most Beautiful Places To Live In New England

Boston, Massachusetts

Boston has exceptional museums, restaurants, and landmarks to visit on a road trip.

Boston is the start for those looking to road trip New England in 10 days; it's one of the oldest cities in the United States and bears much historical significance. Founded in 1630 by John Winthrop , the area was brought forward by Puritans settling in the new country of America.

Today, the capital of Massachusetts is known for its European feel; plus, Boston's many famous landmarks are a major draw for tourists, like the Bunker Hill Monument , the home of Paul Revere, Fenway Park (the home of the Boston Red Sox) , The Freedom Trail , and Boston Common . Visitors to the area can partake in tours of the U.S.S. Constitution , The Boston Tea Party Ships and Museum , and Old North Church .

Boston is known for being quite pricey when it comes to accommodations and entertainment, so it's best to budget accordingly. Parking and traffic can also be a challenge. However, Boston is a walkable city, so it's easy to leave one's vehicle behind and explore on foot.

Cape Cod, Massachusetts

Enjoy fantastic restaurants, hundreds of miles of seashore, and historic museums.

Many look at Cape Cod, Massachusetts, as an idyllic and tranquil seashore destination that allows for adequate relaxation and an opportunity to take in the historical and cultural significance of the area. Located on Route 6A, a historic highway that has achieved National Scenic Byway Status , Cape Cod is home to many different lighthouses, whale-watching recreation, optimal hiking and birdwatching, and multiple art museums.

Those who stop in Cape Cod can particularly enjoy the Cape Playhouse for local theater performances and the Cape Symphony for timeless musical concerts.

• Distance: 70 miles from Boston
• Road Trip Length: Approximately 90 minutes

Providence, Rhode Island

Locals refer to providence as "the creative capital" due to its small-town charm and simultaneous big-city vibes.

Although it is well-known as the smallest state in America, Rhode Island isn't one that should be ignored. The tiny spot on the map packs in over 400 miles of coastline, earning Rhode Island the nickname "The Ocean State" . Located next to the Atlantic Ocean, vacationers will have their fair share of freshly caught seafood to enjoy during their visit.

Besides food, there are plenty of fun things to do in Providence as part of a New England road trip itinerary; stop at the Roger Williams Park Zoo for a day of exploring or go for a ride with Providence Kayak . Locals and guests alike will also appreciate the many local boutique shops and community events.

• Distance: 82 miles from Cape Cod

Related: 10 Beautiful Coastal Stops On A Road Trip In New England

New Haven, Connecticut

The ultimate blend of college town and seaside retreat.

New Haven, Connecticut, is the perfect blend of a college town and a seaside retreat. Younger generations come to advance their education while families, retirees, and vacationers appreciate the beauty the Long Island Sound provides to the area. With the addition of Yale University , the Ivy League establishment has brought multiple museums to the city, including the Yale University Art Gallery, Yale Center for British Art, and the Yale Peabody Museum.

Other points of interest within New Haven include public parks. Two of the most popular recreational areas include East Rock Park and Lighthouse Point Park . Another top contender is Edgerton Park , which is built on a demolished historical estate.

• Distance: 102 miles from Providence
• Road Trip Length: Approximately one hour and 45 minutes

The Berkshires, Massachusetts

Discover this mountain area's museums, orchards, breweries, wineries, and festivals.

There are many small towns and villages that make up the area that is called The Berkshires in Massachusetts. For those looking to learn more about the area, The Berkshires boasts over 100 cultural attractions . People visit the mountain area throughout the year, enjoying various recreational activities in different seasons.

There are many local festivals to take part in during a visit. Depending on the timing of the visit, there are ample orchards, breweries, and wineries to enjoy. Visitors also rave about the local boutique shopping, the Susan B. Anthony Birthplace Museum , Edith Wharton's Home , and Berkshire Art Museum .

• Distance: 78 miles from New Haven

Brattleboro, Vermont

Experience farm-to-table restaurants, a focus on all things local, and beautiful landscapes.

Another one of the fun stops on a New England road trip is the town of Brattleboro, previously known as Brattleborough , which is most commonly known to locals by the simple nickname of "Bratt".

One of the unique aspects of Brattleboro is that it's home to one of the top circus performance schools, NECCA . Visitors can also participate in activities frequently hosted on Retreat Farm ; this farm conservation effort is on 500 acres of forests, farms, trails, and waterways. Whether it's a guided round of "Hike and Seek" or craft beer and cheese tastings, people of all ages are bound to find a suitable activity.

• Distance: 93 miles from The Berkshires

Brattleboro, Vermont, is known as "one of the best small towns in America" and was the winner of the 2023 Strongest Town Award .

Burlington, Vermont

For those keen on ice cream and teddy bears, this stop is a dream come true.

The city of Burlington, Vermont, has an array of attractions to enjoy in a day when visiting as part of a New England 10-day road trip itinerary. The city boasts tons of amenities that suit any age; people can easily pack their days full of fun activities and sightseeing between the beautiful beaches, the various breweries, parks, and shopping centers.

Just a short drive away, road trippers can find the iconic Ben and Jerry's ice cream factory and the Vermont Teddy Bear Factory . Both attractions offer tours for a nominal fee. Visitors should not forget to check out the flavor graveyard at Ben and Jerry's, where the company has laid to rest their retired ice cream combinations.

Plus, a visit to Burlington isn't complete without checking out the Church Street Marketplace shopping center and the scenic overlooks sprinkled throughout the area.

• Distance: 151 miles from Brattleboro
• Road Trip Length: Approximately two hours and fifteen minutes

Related: 10 Cozy Towns To Retire To In Vermont

Bar Harbor, Maine

Although this leg is by far the lengthiest, a pit stop in this coastal town opens up acadia national park.

Home to Acadia National Park, the coastal area of Bar Harbor is outstanding for nature enthusiasts and is easily one of the best stops on a New England road trip route. Visitors have endless opportunities to enjoy hiking, swimming, biking, running, and more during a short stay in Bar Harbor. For those who aren't inclined to participate in such activities, the views of Acadia National Park are also worth the long drive.

Nature aside, Bar Harbor offers much more for locals and tourists to enjoy during their time in the city. The Seal Cove Auto Museum is a top destination, as well as The Natural History Center . Visitors can also enjoy a guided tour of the area through Oli's Trolley and participate in one of the many ghost walks that uncover the past of Bar Harbor.

• Distance: 339 miles from Burlington
• Road Trip Length: Approximately six and a half hours

Portland, Maine

By blending the present with the past, this waterfront city offers a combination of charm and innovation.

Next on the 10-day road trip itinerary for New England is Portland in Maine , which has a history of agriculture and shipbuilding; those two elements are still very present today. Nestled on a peninsula that enters the Casco Bay, visitors will be mystified by the laid-back approach to life that the locals enjoy. The waterfronts are home to many fishing piers that bring fresh seafood to the top-notch restaurants in the city, and the historical homes pay homage to the area's past.

Visitors can hop on a ferry that takes them around Casco Bay. A visit to Portland's many attractions , such as the Portland Observatory and Portland Museum of Art, gives a unique perspective to the cultural scene that is very prevalent in the area. To learn more about the beginnings of Portland, guests should pop into the Maine Historical Society for insight into the early days.

• Distance: 175 miles from Bar Harbor
• Road Trip Length: Approximately three hours

Portsmouth, New Hampshire

Take a break from the car with a visit to this walkable, historic city on the seacoast.

This walkable city on the coast is another one of the fantastic New England road trip stops. As one of the oldest cities in the United States, Portsmouth was settled in the early 1600s by founder John Mason. Today, the area has many attractions that speak to its unique elements and humble beginnings.

Visitors can enjoy the Strawberry Banke Museum, the Seacoast Science Center, and a tour of the Portsmouth Historic Sites, which include the former residences of prominent navy commanders and officials. Other noteworthy activities include a ride on a Portsmouth harbor cruise or taking in a show at The Music Hall.

• Distance: 52 miles from Portland
• Road Trip Length: Approximately one hour

New England Fall Colors Road Trip: Itinerary & Tips

The Magic of Fall Colors: A New England Road Trip Itinerary

As summer fades and the air turns crisp, New England transforms into a breathtaking tapestry of vibrant hues. The leaves, once lush green, burst into a kaleidoscope of reds, oranges, yellows, and browns, painting the landscape with an ethereal beauty that draws travelers from far and wide.

If you’re looking for an unforgettable autumn adventure, a road trip through New England is an absolute must. The region boasts stunning scenery, charming towns, and a wealth of activities to keep you entertained. To help you plan your perfect fall foliage journey, we’ve put together a detailed itinerary, highlighting some of the most popular destinations and hidden gems.

Day 1: The Kancamagus Highway

Start your New England adventure with a drive along the iconic Kancamagus Highway, often referred to as the “Kanc.” This scenic byway winds its way through the White Mountain National Forest, offering breathtaking views of towering peaks, cascading waterfalls, and vibrant foliage. Be sure to stop at several overlooks, such as Sabbaday Falls, Rocky Gorge, and the scenic vista at Conway.

For a unique experience, consider taking a hike on one of the many trails along the Kanc. The moderate-difficulty Bald Mountain trail offers panoramic views of the surrounding mountains, while the easier-going Falling Waters trail leads to a cascading waterfall.

Day 2: Stowe, Vermont

Head south from the Kanc to Stowe, Vermont, a charming village nestled in the Green Mountains. Stowe is renowned for its stunning scenery, particularly during fall foliage season. Take a scenic drive along the Stowe Recreation Path, a paved path that follows the West Branch River and offers stunning views of the surrounding mountains.

Stowe is also a popular destination for outdoor enthusiasts. Hike to the top of Mount Mansfield, Vermont’s highest peak, or take a scenic gondola ride to the summit for breathtaking views. In the afternoon, explore the quaint shops and restaurants of Stowe Village, or visit the Stowe Historical Society Museum to learn about the town’s rich history.

Day 3: The Berkshires

Continue your journey south to the Berkshires, a region of western Massachusetts known for its rolling hills, picturesque villages, and vibrant arts scene. The Berkshires are home to several stunning fall foliage destinations, including the Mohawk Trail, a scenic byway that winds through the mountains, and the Hopkins Memorial Forest, a 2,000-acre forest preserve with hiking trails and scenic overlooks.

For a cultural experience, visit the Clark Art Institute, a world-renowned museum showcasing a collection of European paintings, sculptures, and drawings. In the evening, catch a performance at the Jacob’s Pillow Dance Festival, one of the most prestigious dance festivals in the world.

Day 4: Cape Cod

From the Berkshires, head east to Cape Cod, a peninsula known for its sandy beaches, charming villages, and lighthouses. While Cape Cod is not known for its fall foliage, the region offers a unique and relaxing way to end your New England road trip.

Spend the day exploring the charming villages of Provincetown, Chatham, and Falmouth. Take a walk along the beach, visit a lighthouse, or enjoy a delicious seafood dinner at one of the many restaurants. For a unique experience, consider taking a whale watching tour or visiting a cranberry bog.

Tips for Planning Your New England Fall Foliage Road Trip

• **Book your accommodations in advance:** Fall foliage season is a popular time to visit New England, so it’s essential to book your accommodations well in advance, especially if you’re traveling during peak season (mid-October).
• **Pack for all types of weather:** The weather in New England can be unpredictable, so be sure to pack layers of clothing, including a jacket, hat, and gloves. It’s also a good idea to bring an umbrella or raincoat.
• **Check the fall foliage forecast:** Several websites provide updates on the fall foliage forecast, so you can plan your trip accordingly. Aim to arrive when the leaves are at their peak color, which typically occurs in mid-October.
• **Be prepared for traffic:** Expect to encounter heavier traffic, especially on weekends and holidays. Plan your routes in advance and be prepared for delays.
• **Enjoy the journey:** The beauty of a New England fall foliage road trip is not just about the destination but also about the journey. Take your time, enjoy the scenery, and savor the experience.

With its stunning fall colors, charming towns, and abundance of activities, a New England road trip is the perfect way to experience the magic of autumn. So, pack your bags, grab your camera, and get ready for an unforgettable adventure!

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