Commercial stores and restaurants in the New England town of Brattleboro, Vermont. Image credit jenlo8 via Shutterstock

7 Best Small Towns To Visit In Vermont

Tucked between New Hampshire and New York in the New England region in the northeastern United States, Vermont is a state full of interesting small towns that are waiting to be explored. Known for its natural landscapes, as the Green Mountain State and rich history as the 14th state to join the US, Vermont offers both outdoor recreation and cultural attractions. Many towns throughout the state are all-year destinations, meaning tourists will find a host of activities to partake in, no matter what time of the year they travel to Vermont. From natural paradises and historic sites to bear factories and various wineries, these small towns have something for everyone.

Manchester

Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont.
Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont.

Manchester, Vermont, is a hidden gem nestled between the Green Mountains to the east and the Taconic Range to the west. Travelers might enjoy starting their journey at Hildene, an exquisite Georgian Revival mansion completed in 1905, and the summer home of Robert Todd Lincoln and Mary Lincoln, ending with the breathtaking nature trails in the Merrick Forest. Manchester really is an all-season destination, where travelers are found skiing the slopes of Bromley and Stratton Mountains in the winter, heading to hiking trails up Prospect Rock in spring and summer, and enjoying the vibrant colors of the Battenkill River from canoes in the fall.

For those interested in the arts, the city is home to the Southern Vermont Arts Center, which is a must-visit owing to its various art exhibitions, educational programs, cultural performances, and the Museum of the Creative Process, which brings to light the history of art.

Shelburne

A beautiful farm in Shelburne, Vermont
Farm in Shelburne, Vermont.

Curled up on the shores of the magnificent Lake Champlain, Shelburne is a small town that is only 7 miles south of Vermont’s largest city, Burlington. The town makes for a worthy short getaway due to the tourist-friendly and historic sites it harbors. For nature lovers, Shelburne has a beautiful beach by the lake, maintained throughout the year, and a nature park nearby to take a walk through after boating on the water. Those searching for a more historical experience can take a trip through northern New England’s largest art and history museum, Shelburne Museum, which houses a variety of visual art and culture displays. 

Shelburne also boasts an assortment of touristic experiences to fulfill every traveler’s taste. The Vermont Teddy Bear Factory provides a fun and interactive tour, taking you through the craftsmanship of bear making. For a more unique experience, hop on the Champlain Valley Train ride to explore the scenic countryside of Vermont while enjoying an exceptional dinner. Add the Shelburne Vineyard and Fiddlehead Brewery to the itinerary and encounter local wines and beers to end your vacation in style.

Middlebury

Middlebury Falls in Middlebury, Vermont.
Middlebury Falls in Middlebury, Vermont.

Also situated in the foothills of the Green Mountains, Middlebury is the perfect getaway for those interested in all things nature, culture, and recreation. The brick and stone buildings lining its roads, coupled with the green hills and waterfalls from Otter Creek, seamlessly blend the urban with the country. The city is also close to The Green Mountain National Forest, which has challenging terrain for hikers and bikers looking for a bolder adventure.

Popular writers, such as Robert Frost and Julia Alvarez, lived in this small town, highlighting the city’s culture of art and literature. To this day, there is a regular gathering for writers at Middlebury College’s Bread Loaf Campus. With the Edgewater Art Gallery and Henry Sheldon Museum, the town has a thriving arts and culture scene that tourists can explore. A must-see on a trip to this city should be the sole remaining car-hop restaurant in Vermont, Middlebury's A&W, which is popular with locals and tourists alike. The town is also famous for its seven tasting rooms, which are a delight for those who want to sample the fine beers, spirits, and ciders they produce locally.

Woodstock

Overlooking a peaceful New England Farm in the autumn at early morning, Woodstock, Vermont
Overlooking a farm in autumn, Woodstock, Vermont.

This quintessential New England village is a gorgeous blend of nature, history, and art. With tree-lined streets and restored Georgian, Federal style, and Greek homes, Woodstock is the ideal town to take a leisure walk in. Head to the picturesque Marsh-Billings-Rockefeller National Historical Park to witness the intertwining of history and nature by exploring the historic structures situated amid the park’s vibrant gardens. The Billings Farm and Museum is another similar site that houses a farmhouse that was owned by Laurance Rockefeller Mary French Rockefeller, as well as a museum and an operating dairy farm. 

A tourist-friendly town, Woodstock has free community internet covering most of the village called "Wireless Woodstock" and various festivals throughout the year to keep travelers engaged. The town hosts the annual Bookstock literary festival in June, the annual Harvest Weekend in October, and the annual Wassail Weekend in early December, making this city an all-season destination. It even has various nature activities for all times of the year, such as mountain biking, hiking, golfing, ice skating, and watersports. An interesting spot to visit when in town is the F. H. Gillingham and Sons general store, which still sits in its original historic building established in 1886.

Stowe

Iconic church in Stowe, Vermont with fall colors.
Church in Stowe, Vermont.

Dubbed the “ski capital of the East'', Stowe is a premium resort destination for outdoor recreation. The Stowe Mountain Resort, located on two separate mountains, Spruce Peak and Mount Mansfield, has a lovely ski facility that comes alive in winter. The town also offers a variety of Nordic and alpine recreation in the summer, such as hiking, mountain biking, and rock climbing. The 5-mile paved Recreation Path, recognized nationally, is one of Stowe’s most popular sites for locals and tourists alike. No matter the fitness level, all visitors can enjoy this outdoor space by walking, biking, cross-country skiing, or inline skating on the path.

There are more than 45 hiking trails in the town, much of which are extremely scenic hikes. Travelers looking for a challenge can attempt to hike up Mount Mansfield, which is the highest peak in Vermont. Stowe also has a number of other tourist sites to visit, such as Emily's Bridge, Smugglers Notch, The Current Art Center, and Moss Glen and Bingham Falls.

Brattleboro

A stream flowing through the picturesque town of Brattleboro, Vermont.
Stream flowing through the picturesque town of Brattleboro, Vermont.

The only city with this name in the world, Brattleboro provides a nice mixture of urban and rural atmosphere. Since the town is surrounded by steep hills, most of the houses and buildings are atop the hillsides and bunched together, which brings the cosmopolitan and charming topography together. The Abenaki people who lived and traveled through Brattleboro called this place "Wantastiquet," which means "lost river" or "river of the lonely way" since they believed the town turned its back on its people.

However, Brattleboro is still a town steeped in art and culture, with various art galleries and performance spaces downtown, such as the Brattleboro Museum and Art Center. It also holds a "Gallery Walk" on the first Friday of each month in which artists, galleries, and organizations display new artworks or performances. The Estey Organ Museum is an interesting site to add to the itinerary when visiting Brattleboro. This is an old factory building that houses a variety of organs and pianos on display and the place where Estey organs were originally made.

Putney

Putney General Store vintage sign.
Putney General Store vintage sign.

Listed on the National Register of Historic Places, Putney sits on part of the Connecticut River, approximately 10 miles north of Brattleboro. Its location on the water makes it an ideal getaway for those looking to escape into nature. Drive along Hickory Ridge Road to find some of the most beautiful views in the town, or take a hike through Putney Mountain to appreciate the city’s natural conservation.

An interesting fact to note about the town is that it is home to one of the only accredited colleges built exclusively for learning-disabled students, the Landmark College, established in 1985, making it the first college of its kind. This inclusive and friendly community is also welcoming to tourists, and one of its most popular destinations, Santa’s Land, is visited by people from all over the country. This attraction is a family-friendly theme park where kids can write letters to Santa, indulge in sweets, and even encounter Santa and his elves if they’re lucky. For adults, Putney also has its own local spirits and wines at Putney Mountain Winery and Spirits.

From the shores of Lake Champlain and the ski slopes of Stowe to the artistic heritage of Middlebury and various festivals of Woodstock, the small towns in Vermont are calling explorers to delve into the diversity that Vermont has to offer. Whether you are an outdoor enthusiast or a history aficionado, these hidden treasures are sure to offer something exclusive for your next vacation.

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