The 11 Best Small Towns in Vermont

Warren

This endearing village is smack dab in the middle of the Mad River Valley, a portion of Vermont that is known for its incredible swimming holes, hikes, ski areas, and year-round beauty. In addition to its access to outdoor recreation, Warren has a fun ski town vibe without the unsightly sprawl and trendiness of a ski resort. Instead, you’ll find a handful of local pubs, the Warren Store, and a small number of delightful inns, restaurants, galleries, and shops. 

Bristol

Historic, flat-roofed buildings line Bristol's wide main street, bringing to mind a New England version of an old western town. Bristol’s charm lies in its nod to history (recycling is picked up by horse-drawn wagon), and its delightful modern-day amenities, like art galleries, breweries, restaurants, and the town's country store. Beyond the downtown scene, you’ll find rolling hills and stunning valley views.

Fun fact: Bristol's tradition of holding summer concerts on the village green dates back to the Civil War. 

Newport

Just a few miles from the Quebec border, Newport is nestled along the shore of Lake Memphremagog, a freshwater lake that is shared with Canada (in fact, one can even hop on a boat and sail into Canada for an afternoon!). On the Newport side, you’ll find a waterfront boardwalk, summer concerts, fine dining experiences, and nearby hikes. In the winter, enjoy skiing, snowshoeing, snowmobiling, and a slew of other seasonal sports.

Brattleboro

All the way at the other end of the state on the Massachusetts border, Brattleboro quietly rambles along the banks of the Connecticut River. This quirky town is known for its crunchy food and arts scene, as well as its laid-back, chill vibe. After window shopping downtown, snag a coveted seat at TJ Buckley’s, where you’ll find yourself eating fresh, local food from a chef who creates a menu according to whatever is in season. Planning a visit during the beginning of June? Be sure to catch the annual Strolling of the Heifers (which is exactly what it sounds like: a parade of cows through Brattleboro).

Waterbury

Most visitors to this area are in search of Stowe, a ski town a bit further up Route 100. While Stowe has reason to bring throngs of tourists (especially during its winter season, for its ski resort of the same name), Waterbury is, in its own right, a must-visit small Vermont town. Here you’ll find a much more relaxed, tiny downtown that features world-class dining and drinks. Prohibition Pig is a local favorite where you’ll enjoy live music, smoked meats, and a locavore menu, as well as over 20 craft beers on tap.

Wallingford

This dreamy town is the perfect resting place if you’re aching for a low-key, rural vacation. The quaint village offers food, arts, museums, and plenty of outdoor recreation. With Rutland nearby, you’ll also have access to shopping and dining, as well as a fun nightlife scene. If you’re interested in camping, Emerald Lake State Park is a 20-minute drive south from Wallingford. Here you’ll find a lake that lives up to its name (it’s truly emerald), while a drive up into the wooded hillside will give you secluded camping spots.

Chelsea

Chelsea is not your typical tourist destination. The town gives visitors a feel for how Vermonters truly live, without the hustle of playing to tourists. It also doesn’t hurt that it’s nestled in a gorgeous, albeit sleepy knoll. Every Friday all summer long, you’ll find a bustling farmer’s market, with provisions from many of Chelsea’s local farms (such as Free Verse Farm, an herbal farm with a campground that looks out over the Chelsea valley). There’s also a lovely art gallery, local-food cafe, and a small yoga studio. Downtown’s Chicken Wiggle Farm supplies the town with eggs, meat, and seasonal produce, while farm-curious visitors can enjoy a farm stay at Longest Acres Farm.

Weston

The first time you drive through Weston, you might feel as if you’re on a movie set. This tiny town’s charm is evident in its historic homes and buildings, small galleries and museums, delightful stores and restaurants, and the country store of all country stores, the Vermont Country Store. Although this town has a rustic appeal regardless of the time of year, December truly delivers. Weston’s annual town-wide Christmas celebration features horse-drawn carriage rides, carolers, and a town tree lighting.

Grafton

Included on nearly every list of beloved Vermont towns, scenic Grafton is notable not only for its historic covered bridges and stately Grafton Inn, but also for the fact that with only a year-round population of just over 600 people, Grafton manages to retain a certain relevance. The town is also home to Grafton Village Cheese Co., where one can sample naturally-aged, handmade variations of everything from cheddar to gouda. Stay at the historic Grafton Inn, one of the oldest operating hotels in the U.S., which dates back to 1801.

White River Junction

Most visitors to this region of Vermont are here for Woodstock and just down the road from that lively town is the equally lovely, albeit much smaller and less touristy, White River Junction. This town has recently gone through a bit of a revival—the historic downtown area is also home to a train station, and of course the typical cafes, restaurants, and small shops. A swim in the White River is a must if you are visiting during Vermont’s intensely short but absolutely brilliant summer season. Just ask a local where their favorite swimming hole is, and you’ll be treated to one of the best summer pastimes of Vermont.

Vergennes

Similar in style to Bristol, Vergennes is another flat-front, wide main street type of town, with tiny shops, galleries, and restaurants all in a row. Dating back to 1788, Vergennes was Vermont’s very first city. Although it has grown a bit in size, it still remains small, and many of its oldest buildings are still in working order (such as the still-working opera house, built in 1897, or the Stevens House, a staple since 1793). Dine at the Black Sheep Bistro for a delicious take on Vermont’s famed farm-to-table style restaurants. Located on the banks of the Otter Creek, Vergennes is also close to Burlington, Lake Champlain, hikes, and a myriad of opportunities to enjoy the unparalleled outdoor beauty of Vermont.