15 Best Small Towns to Visit in Vermont - The Crazy Tourist (2022)

New England has a reputation for natural beauty, and Vermont stands out as exceptionally stunning. There is a picturesque charm about Vermont that is difficult to resist. Chock full of small towns, they generally have a village centre, a Main Street, historic architecture, unique boutiques and businesses, and a sense of community that defines its character. Regardless of the season, visitors can enjoy the outdoors, incredible food, and the best that New England has to offer.

Lets have a look at the most charming small towns to visit in Vermont:

1. Chester

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (1)

Source: theculturetrip

Chester has the distinction of having two areas on the National Register of Historic Places. Stone Village, named for the granite buildings there, and the Chester Historic Districts both have traces of colonial architecture and a New England early American aesthetic.

It often serves as base camp for outdoor adventures heading for nearby Mount Killington, Okemo, and Mount Snow. Boaters, cyclists, and ski bums stay in Chester for that small town experience, while taking advantage of the resorts and parks nearby.

One of the most popular activities is a day trip on the Green Mountain Flyer Scenic Railroad. Gorgeous from beginning to end. While you’re there, don’t miss the Stone House Antique Centre, Da Vallia Art, and the Vermont Institute of Contemporary Arts.

2. Woodstock

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (2)

Source: flickr

Woodstock has been a popular tourist destination for years – giving them plenty of time to perfect the quintessential Vermont experience. The town easily combines charming and upscale to provide the escape that you need with all the amenities attached. The boutique and antique shopping is among the best in the state, the dining options are incredible, and the entertainment is almost endless.

History buffs will enjoy the Billings Farm and Museum. Once owned by Laurence and Mary French Rockefeller, the farm is now a dairy with a restored late 19th century farm house – both National Historic Landmarks. Art lovers will enjoy the many galleries (top pick: Stephen Huneck Gallery), and foodies will want to spend a day in F.H. Gillingham & Sons. This is a general store and gourmet shopping experience not to be missed.

3. Montpelier

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (3)

Source: flickr

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America’s smallest capital is Montpelier, Vermont. Among the locals (and all Vermonters consider themselves local) it’s known for its many farm-to-table restaurants, and daily farmers market.

As the centre of government for the state, there is a little something of everything here. Visit the Vermont Historical Society Museum, the state house, Hubbard Park, the New England Culinary Institute, and T.W. Wood Art Gallery.

And that’s just a start! Make no mistake, this is still a small town, with the kind of hospitality and charm you expect. But with such a thriving cultural scene, Montpelier is something special.

4. Brattleboro

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (4)

Source: flickr

Located in the southern part of the state, Brattleboro has a funky, crunchy, arts vibe that attracts people from all over the region. It’s a walkable town with tons of clubs, restaurants, studios, galleries, and shops. Its contemporary atmosphere is balanced by the beauty of Mother Nature.

There’s a gorgeous mountain or river view no matter where you are in town. When you’re out walking, an impromptu street performance is not out of the question, and you’ll love stopping at the independent bookstores, record shops, and crafts boutiques.

The town has several theatres, many with historic significance. Every month there’s a First Friday Gallery Walk and almost every restaurant exhibits local artists. Brattleboro is a town that will have you talking about it for a long time after.

5. Putney

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (5)

Source: flickr

A few minutes from Brattleboro is Putney. It’s got a similar vibe, but even more laid back. Check out the spinnery, the berry and apple orchards, and the winery while you’re there. This is a place for slow walks and deep breaths.

It’s the kind of place you don’t tell people about because you don’t want it to ever change. Sacketts Brook still has its original stone arch bridge and flows right through the centre of town. Putney general store and co-op are community staples. It’s that kind of town.

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6. Lincoln

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (6)

Source: flickr

At the bottom of Mount Abraham is Lincoln. The natural surroundings along the New Haven River will take your breath away. The residents take pride in the beauty of the farms and forests in the area. Settled by Quakers in the late 18th century, there are about 1200 residents now.

Lincoln is best known for its interesting treehouse. Built across four large maples and 30 feet up from the ground, you can stay there for $150 per night – complete with heat, shower, electricity, and even a mini fridge. Don’t forget to visit the Old Hotel, the general store, and Burnham Hall.

7. Bristol

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (7)

Source: flickr

This is the place for festival lovers. They’ve got a celebration for everything, and people come from all over the state for the Outhouse Race – the longest running one in the country. All of downtown is listed as a National Historic District and you’ll definitely feel that you’ve stepped back in time.

Bristol is located in the foothills of the green Mountains and makes the perfect getaway spot. Visitors love the village shops and the friendliness of the locals. If you’re around in June, don’t miss the Pocock Rocks Street Fair or the Bristol Band summer concerts (which have been happening since the end of the Civil War).

8. Stowe

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (8)

Source: flickr

No matter the season, Stowe is a prime destination in Vermont. Thanks to Stowe Mountain Resort there are outdoor adventures just waiting to be had. Mount Mansfield is the tallest peak in Vermont and it’s a mecca for nature enthusiasts. Ski, hike, or return again and again to do both.

The village itself is 200 years old and downtown you’ll find museums, galleries, theatres, outdoor film festivals, the Vermont Ski and Snowboard Museum, and plenty of fine dining. It’s year round beauty make it one of the absolute must-visit towns.

9. Waterbury

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (9)

Source: wikimedia

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When Vermonters need to get away from it all, they go to Waterbury. Often described as a sleepy town, Waterbury is a low key, low profile kind of town. Town pride is cantered around locally sourced fine dining.

Its undoubtedly the best of the best of Vermont. Because of the fantastic natural settings, Waterbury is a popular wedding destination. For top of the line accommodations, try Groenberg Haus, a chalet on a hilltop, complete with a stone hearth and grand piano.

10. Shelburne

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (10)

Source: flickr

Looking for luxury? On the shores of the scenic Lake Champlain sits Shelburne – a suburb of Burlington. People come to be pampered and to splurge. Home to the Shelburne Museum, Shelburne Farms, and the Vermont Teddy Bear Company, it’s also a family destination.

The farm boasts a one-hundred room guest house, a five storey barn, hayrides and a wonderful hiking trail. At the museum you can see live printing, blacksmithing, and weaving demonstrations. The lake front beach is a perfect spot in the summer and several companies have boat rentals. If it’s apple season, head over to Shelburne Orchards for the tastiest apples and cider in Vermont.

11. Manchester

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (11)

Source: flickr

Calling all shoppers! Don’t miss out the factory outlets and other spectacular shopping opportunities in Manchester. This is where New Yorkers, and Europeans in recent years, come for the best select and great deals. From high end retail, charming boutiques, and all out bargains, you won’t be able to stop.

Manchester also has a fantastic cultural scene. Enjoy concerts, galleries, theatre, history, crafts, and artisanal dining. The village blends cultural sophistication with old-world New England charm for an incredible experience from beginning to end.

12. Grafton

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (12)

Source: flickr

Long ago, Grafton was the major stagecoach stop between Albany and the Green Mountains. They’ve been hosting visitors for almost two centuries. Located in the mountains, many of the original buildings have been restored to provide an authentic New England feel.

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As you walk downtown you’ll feel like you’re walking in a museum. In the winter, the snow covered mountains provide an ethereal ambiance that is unique to Grafton. The 600 residents all regularly participate in town hall meetings and work together to create a vibrant and lovely community.

13. Grand Isle

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (13)

Source: flickr

Grand Isle is about 35 square miles – almost 19 of which are water. Located in the Islands and Farms region of the state, Grand Isle is a fishing town. The Ed Weed Fish Culture Station is located here, one of only five in the state. The oldest log cabin in New England is also here. Hyde Log Cabin was built in the late 18th century and was home to the Hyde family for over 150 years.

The most visited state park is in Grand Isle. It’s the second largest in Vermont, with RV camping and primitive camping. The experience here is slightly different than the rest of the state, thanks to the abundance of water and the fishing culture. That’s the perfect reason to add it to your list. It’s another Vermont one-of-a-kind.

14. Charlotte

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (14)

Source: flickr

Synonymous with the Champlain Valley is Charlotte. Established in the late 18th century, the growing town is primarily agricultural. Orchards, dairies, sugar bushes, berries, honey, livestock, and grain are all flourishing economies here. Charlotte even has a winery that received high praise from those who visit.

Mount Philo State Park (named for the almost 1000 foot peak) is another popular park with wonderful vistas, trails, and a nearby wildlife refuge.

15. Craftsbury

15 Best Small Towns to Visit in Vermont - The Crazy Tourist (15)

Source: flickr

Picture rolling hills, picket fences, family farms, and green forests. You’re seeing Craftsbury, Vermont. Made up of five villages with a combined population of about 1,200, the town is classic Americana.

Come for cross country skiing and snow mobiling in the winter, maple sugaring in the spring, the Antiques and Uniques Festival in July, and stunning fall foliage each autumn.

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Where to stay: Best Hotels in Vermont (VT)

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FAQs

15 Best Small Towns to Visit in Vermont - The Crazy Tourist? ›

15 Best Small Towns to Visit in Vermont
  • Chester. Source: theculturetrip. Chester, Vermont. ...
  • Woodstock. Source: flickr. Woodstock, Vermont. ...
  • Montpelier. Source: flickr. Montpelier, Vermont. ...
  • Brattleboro. Source: flickr. Brattleboro, Vermont. ...
  • Lincoln. Source: flickr. ...
  • Stowe. Source: flickr. ...
  • Shelburne. Source: flickr. ...
  • Grafton. Source: flickr.

What is the quaintest town in Vermont? ›

Grafton[SEE MAP]

Grafton, considered one of Vermont's prettiest towns, got its name in a unique way. Originally known as Thomlinson, the right to rename it was auctioned in 1791 for $5 and some rum; the winning bidder named it after his home town of Grafton, Massachusetts.

What is the coolest city in Vermont? ›

1. Stowe. Name a Vermont icon and Stowe probably has it: a white-spired church, a mountain laced with ski trails, bucolic farms, a covered bridge. With the combination of beautiful mountain scenery, year-round outdoor sports, and a lively arts and dining scene, there's something for everyone in this pretty town.

What is the best month to visit Vermont? ›

That's why the best time to visit Vermont is the fall, between September and November! This time of year, the average temperature is between 46°F and 69°F, making for beautiful weather. There's usually not a lot of rain in the fall, but there are crisp winds. Truthfully, it's the perfect sweater weather in New England.

What is Woodstock VT known for? ›

Woodstock, Vermont is a picture-book New England Village, voted the prettiest town in America. world heritage farm, great restaurants, eclectic boutiques and down-to-earth Vermont Hospitality.

Is Ludlow Vt worth visiting? ›

One great spot to do just that is tiny Ludlow, Vt. Ludlow is home of the popular Okemo Mountain Resort and, indeed, the mountain trails jut out above the village. The town feels tucked in below all that skiing and riding splendor, but those who visit know it has plenty to offer the non-skier as well.

Is Rutland VT worth visiting? ›

Colorful, Historic, Festive

Rutland is home to a picturesque historic downtown rich with community events, arts, and character and is conveniently located in central Vermont close to several mountains and lakes.

What is the number one tourist attraction in Vermont? ›

Unquestionably Vermont's most popular tourist attraction for children, Ben & Jerry's factory tour is a favorite experience for adults, too.

What is the safest town to live in Vermont? ›

1. Shelburne. Welcome to the safest city in Vermont, Shelburne, sitting peacefully near Lake Champlain, at the northwest border of the state.

What is the most diverse town in Vermont? ›

Winooski. #1 Most Diverse Places to Live in Vermont.

Where should I vacation in Vermont in the summer? ›

Top 10 Family Summer Vacation Getaways in Vermont
  • Burlington. Church Street Marketplace in the historic district of Burlington, Vermont. ...
  • Dorset. Credit: dougtone via Flickr. ...
  • Manchester. ...
  • Newport. ...
  • Bennington. ...
  • Middlebury. ...
  • Montpelier. ...
  • Grand Isle.

Where is the nicest place to live in Vermont? ›

Surrounded by beautiful mountains, diverse weather and quaint small towns, Vermont makes a great place to raise a family.
...
As a renowned Vermont real estate company, here are the top 5 Vermont towns to live in.
  1. Montpelier, VT. ...
  2. Barre, VT. ...
  3. Northfield, VT. ...
  4. Stowe, VT. ...
  5. Woodstock.
Jul 31, 2021

What is the most affordable place to live in Vermont? ›

St. Albans topped the list for Vermont. The median income for the area was shown to be $53,647.

What is the most popular food in Vermont? ›

Vermont is known for foods like Vermont cheddar cheese, maple syrup and the ever-popular Ben and Jerry's ice cream. It is also home to many farms, artisan foods, fresh produce, wineries and breweries. Find local products at Vermont Farmers' Markets and farm stands in all seasons.

What is the coldest month of the year in Vermont? ›

The cold season lasts for 3.3 months, from December 3 to March 13, with an average daily high temperature below 38°F. The coldest month of the year in Burlington is January, with an average low of 14°F and high of 29°F.

What's the best time to visit Burlington Vermont? ›

The best time to visit Burlington is from May to September when the festival schedule picks up and the city bursts with greenery. The shoulder months of April and November welcome fewer crowds and reduced hotel rates but are less desirable for adventure travelers.

Is Woodstock worth visiting? ›

In reality, Woodstock is a charming little Catskills oasis where fewer than 6,000 residents prop up an art, religion, music, and theater scene worthy of national attention. Whether you're visiting for a day, weekend, or entire week, the 2-hour drive from NYC to Woodstock will prove worth it.

What is Manchester Vermont known for? ›

Only a four-hour drive from Manhattan and a two-hour drive from Boston, Manchester is easily accessible for a three-day vacation while also embodying the quintessential Vermont town with white church steeples, local breweries, fantastic restaurants, dynamite art galleries, and many other attractions.

Where do you fly into for Woodstock VT? ›

The nearest airport to Woodstock is Lebanon (LEB) Airport which is 10.5 miles away. Other nearby airports include Burlington (BTV) (66.8 miles), Manchester (MHT) (73 miles), Albany (ALB) (89.5 miles) and Portland (PWM) (111.1 miles).

What is the poorest city in Vermont? ›

Ferdinand is a town in Essex County with a per capita income average of $9,138, making it the poorest town in Vermont.

What's the poorest County in Vermont? ›

Chittenden

What is the poorest County in Vermont? ›

Chittenden County's poverty rate of 9.6 percent is second lowest in the state. The highest poverty rates are in the Northeast Kingdom and in Rutland, Windham, and Bennington counties. In southern Vermont only Windsor County does not have a high poverty rate.

Are there any abandoned towns in Vermont? ›

Yes, there are. Lewiston and Somerset are two small towns in Vermont that are known for being ghost towns.

What is Manchester Vermont known for? ›

Only a four-hour drive from Manhattan and a two-hour drive from Boston, Manchester is easily accessible for a three-day vacation while also embodying the quintessential Vermont town with white church steeples, local breweries, fantastic restaurants, dynamite art galleries, and many other attractions.

What towns are near Stowe Vermont? ›

Cities near Stowe, Vermont:
  • Morristown, VT.
  • Waterbury, VT.
  • Montpelier, VT.
  • Jericho, VT.
  • Williston, VT.
  • Barre, VT.
  • Northfield, VT.
  • Hinesburg, VT.

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