15 Charming Small Towns in Vermont Not to Miss


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New England is filled with charming towns, and Vermont is no exception. Filled with breathtaking green mountains, rich history, and some interesting foods (maple creemee, anyone?), Vermont is one place that should be at the top of your travel list.

No matter what time of year you visit, you’re in for a treat! While the most popular time to visit Vermont is during autumn to see the fall foliage, you can avoid the crowds of leaf peepers by visiting during the ski season, springtime, or summer.

To help you plan your next trip to the home of Ben & Jerry’s, I’ve compiled a list of the top must-see charming small towns in Vermont that you won’t want to miss!

Most Charming Small Towns in Vermont

Williston

View of Mount Mansfield at sunset
Charming Vermont towns like Williston are lovely vacation destinations.

Located in northern Vermont near Burlington, Williston is known for being a charming suburb. Historically, Williston was originally farmland but has become a bustling place to live since. It’s an effortless place to get to since it’s located near I-89 and can be a suitable place to base yourself if you want to explore Burlington.

This charming VT town is filled with many outdoor areas to explore, including Lake Champlain, Lake Iroquois, and the Green Mountains, which are impossible to miss. There are year-round outdoor activities in Williston, which makes it an adventure lover’s dream. Pass time hiking, swimming, kayaking, snowshoeing, and more in one of the most beautiful towns in Vermont. 

If you fancy a bite to eat, be sure to stop by the Vermont Tap House, a favorite among locals. They’re most well-known for delicious wood-fired pizza and serve up 36 different craft brews, and source most of their ingredients from local farmers. Their late-night hours make it the perfect place to grab a delicious meal no matter the time!

Dorset

A white building with black shutters and green awnings
Editorial credit jenlo8 | Shutterstock.com; so much Vermont small-town charm in Dorset!

Next up: Dorset! This charming small town in Vermont is located in the southern part of the state in Bennington County. With an average population of 200, this is the perfect place to get acquainted with locals and experience real Vermont small-town life. 

Dorset Vermont is most well known for being home to the Dorset Marble Quarry, a popular cliff-jumping location among locals. It’s also historically significant to the United States, as it was the country’s first-ever marble quarry! It’s located right off Route 30 and is a great place to cool off during a hot day.

Emerald Lake State Park is also in Dorset, the perfect place to go canoeing or kayaking. Plus, there are quite a few hiking trails here, so you can go out and explore the outdoors. When visiting Dorset, opt to stay in a bed and breakfast to support a local family and have a unique experience in this charming town.

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Grafton

A snow-covered gazebo
When it comes to picturesque towns in Vermont, Grafton makes the list and then some!

Another charming town to visit in southern Vermont is Grafton! It’s genuinely one of the prettiest places in all of New England, located right in the Green Mountains. 

There are tons of fun outdoor activities to partake in while visiting Grafton. The most popular spot to visit is the Grafton Ponds Outdoor Center. This is a great place to go biking, hiking, snowshoeing, and even cross-country skiing.

One spot that can’t be missed is the Phelps Barn Pub, which offers weekly specials for burgers and beers. Locals and tourists alike agree that it’s one of the best burgers in the world. It’s located in the lovely Grafton Inn, so if you’re looking for cute places to stay in Grafton that have a great onsite restaurant, this is it!

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Woodstock

White wooden house next to a covered bridge
Is Woodstock the most beautiful town in Vermont? Quite possibly!

This list of charming Vermont towns would not be complete without at least mentioning Woodstock. Known as being one of the most picturesque small towns in the whole state, Woodstock can not be missed during a trip to the Green Mountain state.

If you’re lucky enough to be visiting Woodstock during winter, you absolutely must head to Saskadena Six. While it’s technically located in South Pomfret, it’s incredibly close to Woodstock and is a top spot for skiing and snowboarding. It has trails for all levels, so even if you’re entirely new to the outdoor sports scene, you’ll be able to fit right in. 

Some other popular spots to visit in Woodstock include the Billings Farm and Museum (a must-visit to learn about 19th-century New England life), the Marsh-Billings-Rockefeller National Historical Park, and the Middle Bridge. When you’re ready to take a break from all the activities, be sure to stop by the Mountain Creamery for a bite to eat!

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Manchester

If you’re looking for the best small towns to visit in Vermont, Manchester will be on that list every time. There are so many cute small town things to do in Manchester, like searching through The Northshire Bookstore, one of the top independent bookstores in New England, for all kinds of great VT souvenirs, including what may become your new favorite book.

Visit Hildene, the historic estate of the only Lincoln child who survived to adulthood, and hike some of the top Manchester trails to really immerse yourself in the beauty of this area of Vermont. There are some great options for restaurants in Manchester, too, and if you’re looking for a great place to stay, check out The Kimpton Taconic Hotel in historic Manchester Village for the perfect blend of Vermont rustic elegance!

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Chester

Aerial view of mountains and fall trees
Chester is one of the best small towns to visit in Vermont.

Located in southern Vermont’s Windsor County, Chester is an absolute must-visit charming town, especially in the summer or winter because of all the fun recreational activities available.

There are tons of winter sports areas near Chester, including Okemo Mountain Resort, Bromley Mountain, and Stratton Mountain Resort. All are equally fun! Are you not into outdoor sports? Luckily, Chester is also home to lots of great places to shop. Some of Chester’s top stores include Blair Books, Stone House Kettle Corn Company, and Smokeshire Design.

If you have more time while visiting Chester, be sure to stop by Endless Creations Pottery Studio. This fun art studio is excellent for all ages. They offer classes on wood burning, pottery, jewelry, and more. Of course, their most popular activity is pottery painting! What’s even better is you don’t have to make a reservation; they accept drop-ins!

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Brattleboro

Brattleboro is such a cute town in Vermont, it has pretty much all the things people think of when they come to visit and experience Vermont charm: you’ve got a cute downtown, interesting museums, art galleries, indie bookstores, great restaurants and places to stay, and fun festivals that are quirky and unique, like their annual Strolling of the Heifers.

This fun event includes an actual parade of adorable baby cows strolling along adorned with flower garlands and crowns, meant to celebrate the connection between farm and community. Brattleboro is also home to the picturesque Creamery Covered Bridge; as if you needed another reason to visit this idyllic VT town!

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Waitsfield

Aerial view of a town in Vermont
Waitsfield is a sweet town in Vermont.

Waitsfield is a town near Montpelier that’s extraordinarily picturesque and offers impressive scenic views of the surrounding area. While the most popular time to visit Waitsfield is during the winter because of its proximity to the Mad River Glen Ski Area, it’s gorgeous any time of year.

Wondering what to do in Waitsfield? Be sure to check out Hartshorn Organic Farm. Not only are there farm tours available to visitors, but there are also food festivals, workshops, and more. You’ll even be able to learn all about the maple syrup process by visiting their maple sugar house!

If you’re wondering where to stay, opt to reserve accommodations at The Round Barn! This beautiful bed and breakfast is situated on 245 acres of land and is a great place to explore around. There are ponds, gardens, and of course, areas to go hiking and snowshoeing.  The Round Barn is a great place to stay for family and couples alike.

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Bennington

Beautiful Bennington is one of those quaint Vermont towns that might just make you want to give up big city life for small town Vermont living! Not only can you find the usual Vermont charm with great farm to table restaurants, scenic hiking trails, cute shops, and historic monuments, but Bennington is also home to The Apple Barn, one of the cutest little country bakeshops in all of New England.

Swing by the Apple Barn for some of their famous apple cider donuts and a jug of their apple cider and take home some of that Vermont fall flavor. Oh, and be on the lookout for the blue moose, you’ll see what I mean! There’s plenty to see and do in beautiful Bennington, so put it on the list of must visit small towns in Vermont.

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Shelburne

A view of a lush green hillside with a lake in the distance
Just look at this idyllic Vermont scene!

Located right on Lake Champlain, Shelburne is one of the most-visited charming towns in Vermont, and for a good reason. While it’s one of Burlington’s suburbs, it’s still filled with tons of fun activities for all ages.

The top place to visit here is Shelburne Farms. They host a variety of fun activities and workshops to teach visitors all about how farm-to-table works! Plus, they offer a variety of delicious maple syrup and Vermont cheeses.

To learn more about Shelburne, be sure to stop by the Shelburne Museum. It was founded in the mid-20th century and includes exhibits covering both art and design between 39 different buildings. You could easily spend a whole day exploring here! If you find that you have more free time in Shelburne, some other great places to visit include the Vermont Teddy Bear Factory (perfect for families!), the Shelburne Vineyard, and Fiddlehead Brewing Company.

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Rutland

Rutland is such a cool Vermont town to visit, with a unique claim to fame: it is home to the oldest continuously published newspaper in Vermont, The Rutland Daily Herald. Don’t worry, if you’re not pulled in from its press prowess, there’s plenty more! This cute little VT town is also home to an adorable downtown with a great art scene, including gorgeous murals on several buildings downtown and a Sculpture Stroll to follow, as well.

There’s also great hiking nearby and a beautiful lake to enjoy in the warmer months, so there’s plenty of that gorgeous Vermont eye candy to see and explore. You’ll also find a nice little restaurant selection in this cute VT town, so come to Rutland expecting to find just about all the Vermont charm you could possibly want.

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Stowe

A white church surrounded by fall trees in the mountains
Stowe is hands down one of the prettiest towns in Vermont.

Stowe is yet another incredibly charming and picturesque Vermont town located in the northern part of the state. It’s right next to the highest mountain peak in the whole of Vermont, Mount Mansfield, which is a popular destination for tourists.

This town is an outdoor lover’s dream, mostly because it’s where Smuggler’s Notch State Park is located. This is a popular spot to go for skiing and snowboarding in the winter, but also camping, hiking, and more in the summer. It’s enjoyable for all ages, with great restaurants and hotels, too.

While this list is filled with tons of great places to visit in Vermont filled with charm, Stowe is one place you surely can’t miss. The famous von Trapp family (yes, from The Sound of Music) moved to Stowe to escape Austria during the Nazi era. Now it’s home to the Trapp Family Lodge, which is filled with a rich history.

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Wilmington

Mountains in Vermont in the fall
One of the best little towns in Vermont, Wilmington is very cute!

Wilmington is an incredibly charming town located only a half hour away from Bennington. This village is gorgeous, and while it faced a lot of devastation after Hurricane Irene, it has had a comeback in the past few years.

The perfect way to spend the day is by exploring the downtown area. There are tons of great restaurants in the downtown area, especially Dot’s, a fun diner that offers delicious and affordable eats. Visiting over the weekend? You’re in luck! There’s a great flea market held in Wilmington with local vendors selling a wide variety of souvenirs, local foods, crafts, and more.

If you’re more of an outdoor enthusiast, then be sure to check out some of the local hiking trails. Popular ones include the Valley Trail, Hogback Mountain Trails, and the Hoot, Toot, and Whistle Trail. Some of these are easier than others, so make sure you do some quick research online before choosing the perfect hike for you! Each one offers rewarding views that you won’t want to miss.

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Middlebury

This cute little college town is definitely one of the prettiest towns in Vermont, and one with plenty to do, too! With a beautiful downtown, a classic white steepled church, lovely, well-kept parks and green spaces, and even a ski area in town limits, Middlebury is a very charming Vermont town to visit!

In the warmer weather months, hop on a bike or head out on foot to walk part of the TAM or Trail Around Middlebury, a 16 mile scenic stroll all around this cute VT town. In the colder months, head out to ski or snowboard at the Middlebury Snowbowl. Indoors you’ll find shopping, restaurants, theatre, and more, so Middlebury is a Vermont town with something for everyone!

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Weston

A waterfall and a mill
Weston is full of small town charm like this!

Last but not least is Weston! This small but charming Vermont town is the perfect place to base yourself to explore the rest of the breathtaking and scenic Green Mountain National Forest.

Theatre fans are in luck because Weston is home to The Weston Playhouse, the oldest theatre company in the whole state. The majority of shows and musicals are on during the summer and are always exceptionally well produced. Plus, The Weston Playhouse has even been nationally-recognized by Playbill, The New York Times, and The Wall Street Journal.

For a bite to eat, be sure to head to some local favorites, including the Village Green Gallery Coffeebar, The Vermont Country Store, or the Moose Lounge. Each is equally amazing and serves up delicious eats!

Whether you plan on visiting Vermont for a weekend, a road trip, or a week-long getaway, you’ll have the time of your life. You might even be able to visit more than one of the towns on this list during one trip if you plan your time wisely!

Now, what are you waiting for? Start planning your next trip to one of Vermont’s cutest towns!


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