Burlington, Vermont: Church Street Marketplace at twilight.

8 of the Most Walkable Towns in Vermont

Vermont may be a small state, but what it lacks in size, it makes up for in character. Particularly noteworthy are the numerous walkable small towns throughout the state. These small towns are naturally beautiful and welcoming and offer visitors the chance to explore quaint coffee shops, charming bookstores, and historical wonders on foot. Explore eight of the most walkable towns in Vermont and what makes each one unique.


Church Street in Burlington, Vermont.
Church Street in Burlington, Vermont.

Vermont’s largest small town, Burlington, is nestled along the shores of Lake Champlain. It has many residents, 44,448 to be exact, and offers visitors unique and memorable experiences. A few walkable highlights include Church Street Marketplace, Waterfront Park, and Flynn Center which are all within minutes of each other. Church Street Marketplace is a pedestrian-only zone where visitors can dine and shop. At The Waterfront Park, visitors can enjoy the views of the Adirondack Mountains and Lake Champlain, and bike or stroll along the path. Lastly, the Flynn Center is a performing art theater where visitors can catch a show.


Autumn town skyline of Montpelier, Vermont, USA.
Autumn town skyline of Montpelier, Vermont.

As of 2024, Montpelier has 7,979 residents. It is Vermont’s state capital and one of the smallest state capitals in the U.S. Built in 1859, the Vermont State House is Montpelier’s crown jewel. Located behind this historic building is Hubbard Park. It is a 200-acre park with a stone observation tower, walking trails, and a forest that overlooks the town. Once visitors are done exploring these sites, they can walk to eateries like Skinny Pancake, North Branch Cafe, Positive Pie, and Mad Taco to grab a delicious bite.


Two Adirondack chairs overlooking Vermont foliage at Middlebury College.
Two Adirondack chairs overlooking Vermont foliage at Middlebury College.

Middlebury is a college town with several trails and waterfalls. The Green Mountains are to the East, Chipman Hill is to the north, and to the west is Otter Creek. The town is equal parts tranquil escape and bustling college town. While in town, visitors can take a tasting along a five-mile trail of distilleries, breweries, and vineyards, beginning at Lincoln Peak Vineyard. The Trail Around Middlebury is the best way to tour the entire town on foot. It is a 16-mile path that encircles the town with access points to the Green Mountain National Forest trails and the Long Trial.


Aerial view of Stowe, Vermont, and the Green Mountains with autumn colors.
Aerial view of Stowe, Vermont, and the Green Mountains with autumn colors.

Situated in Northern Vermont, Stowe is a popular destination because Mount Mansfield overlooks the town. Skiing, biking, rock climbing, and hiking on the mountain are popular activities. At the base of the mount lies the Smugglers’ Notch State Park. The park has a campground, wetlands boardwalk, picnic area, and a 272-mile-long trail. Downtown Stowe is walk-friendly with the Stowe Community Church which was built in 1863, being its focal point. Not too far from downtown Main Street is Sunset Rock; it is a short, easy hike that offers visitors beautiful views of the town below. Stowe is also the birthplace of the popular ice cream chain Ben and Jerry’s.


Brattleboro, Vermont, USA: Spring aerial photo of the town on a partly cloudy day.
Spring aerial photo of Brattleboro, Vermont. Editorial credit: SEALANDSKYPHOTO / Shutterstock.com

Brattleboro is a town in Southern Vermont where the Connecticut River flows. It has a population of 11,894 people and is a very walkable town. Visitors can start their tour on Main Street, stopping at the Brattleboro History Center and Museum. Other stops include the 1930s Latchis Hotel and Theater and the Brattleboro Museum and Art Center, formerly a railroad station. After the tour, visitors can grab a bite to eat at popular eateries such as Amy’s Bakery Arts Cafe, located on Main Street. The best time to visit is between June and October when the walking trails are accessible and when the town hosts several annual summer events such as the Farmers Market.


Early autumn foliage scene of houses in the mountains of Woodstock, Vermont.
Early autumn foliage scene of houses in the mountains of Woodstock, Vermont.

Often described as one of America’s prettiest towns, Woodstock is home to 3,024 people. There are several walking tours for visitors to choose from. Begin your journey at the Ottauquechee River Trail. It is an outdoor path that offers breathtaking views of the Ottauquechee River. A 3-mile long trail starts at East End Park where visitors can picnic or catch a show at the outdoor amphitheater. The Marsh-Billings-Rockefeller National Historical Park is another walkable site that is home to ancient hemlock trees, carriage trails, and the stunning Pogue Pond.


Bennington, Vermont, USA: Quaint boutiques and specialty restaurants in the downtown district.
Bennington, Vermont: Downtown district. Editorial credit: James Kirkikis / Shutterstock.com

Bennington is home to 15,272 people, and the town is steeped in history. The best place to walk around in Bennington is downtown, beginning on South Street at the Welcome Center, with on-site parking. The self-guided tour explores South Street, Putnam Square, and the Walloomsac River. The Welcome Center is a historic site built in the 1830s or 40s as a field stone blacksmith shop. Other stops on the tour include the Bennington County Courthouse, constructed in 1936; a scenic river walk along Walloomsac River; and a stop at Vermont Federal Bank, a white marble building built in 1930 with an Italian marble interior.


Manchester, Vermont: Exterior architecture and landscaped gardens of Hildene, The Lincoln Family Home, open to the public.
Manchester, Vermont: Hildene, The Lincoln Family Home. Editorial credit: Theresa Lauria / Shutterstock.com

Founded in 1791, Manchester is a historic New England town with 4,501 residents. It is an especially walkable town with most visitors taking a guided tour through three neighborhoods: Manchester Depot, Manchester Center, and Manchester Village. The Manchester Historical Society offers hour-long self-guided tours that take visitors through the town and explain its history. Visitors will pass by an 18th-century farmhouse, the Victorian-style Charles Orvis Inn (built in 1833), the Mark Skinner Library, the historic Soldier’s Monument, and the Burr and Burton Academy - a day school established in 1829.

Explore Vermont's Walkable Charms

When planning your next vacation, put your best foot forward and step into the charm and beauty of Vermont by exploring these eight most walkable towns. From Bulrington’s vibrant streets to Montpelier’s natural beauty and Woodstock’s historic charm, each of these towns offers grand adventures that are best explored on foot. These walkable towns allow visitors to immerse themselves in the picturesque landscapes and rich heritage of Vermont while making lasting memories.

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