Summary
- Vermont’s downtown areas showcase the state’s distinct character, offering shops, art galleries, and regional culture. Enjoy a getaway during the fall.
- Burlington boasts a lively downtown district with scenic lake views, pedestrian-only shopping, and dining options. Don’t miss Waterfront Park.
- Explore the picturesque town centers of Manchester, Shelburne, Stowe, Waitsfield, Brattleboro, Middlebury, Barre, Woodstock, and Dorset for charming architecture, shopping, and attractions.
With its quaint villages, charming downtown, and abundant natural beauty, Vermont offers plenty of picturesque towns to explore in the fall. The downtown areas of these spots showcase Vermont’s distinct character, from bustling small cities to historic rural towns.
Travelers can browse local shops and art galleries, dine at acclaimed restaurants, and soak up the regional architecture and culture. The Green Mountain State’s distinctive downtown allows visitors to experience the heartbeat of quintessential Vermont. Whether strolling along vibrant main streets or relaxing in cozy village greens, the most beautiful downtown areas in Vermont showcase why many people simply love to enjoy a getaway in this state, especially during the fall.
10
Burlington
View of Church St, Burlington, Vermont, U.S.
Perched along the shores of stunning Lake Champlain, Vermont’s largest city, Burlington boasts a lively downtown district. Walkable streets with shops and eateries lead down to the vibrant waterfront area.
The Church Street Marketplace offers pedestrian-only shopping and dining with street performers and events. Enjoy gorgeous lake views from Waterfront Park (home to one of the most beautiful lakes in Vermont) and snap photos of the Burlington Boathouse.
- Hours: Church Street Marketplace shops/restaurants are generally open daily, 10 am-9 pm. Waterfront Park is available 24/7.
- Things to Do: Stroll the lakefront path, enjoy a sunset over Lake Champlain, and browse Church Street shops.
- Top Attractions: Waterfront Park, ECHO Leahy Center, Church Street Marketplace.
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Manchester
The Hildene, The Lincoln Family Home in Manchester, Vermont
Set amid the mountains of southwestern Vermont, the picturesque village of Manchester charms visitors with its restored colonial architecture and upscale shops. Meander along quaint Main Street and visit independent boutiques, art galleries, cafes, and inns.
Stop by the American Museum of Fly Fishing or visit the historic Hildene Estate, the Lincoln family home. Relax by the town’s charming roundabout and marble fountain in the center of town.
- Best Time to Visit: Summer and fall to enjoy the outdoors, foliage, and summer theatre. Many attractions closed in winter.
- Top Attractions: Hildene House, American Museum of Fly Fishing, Southern Vermont Arts Center.
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Shelburne
Buildings and cityscape of Shelburne, Vermont, USA
Situated just south of Burlington along Lake Champlain, Shelburne’s quaint downtown offers fabulous lake views and attractions. Stroll along the tree-lined village green and browse the cafes, cheese shops, and craft stores lining Shelburne Road. Wander to the waterfront and Shelburne Shipyard area with restaurants, shops, and walking paths.
Don’t miss the nearby Shelburne Museum and Shelburne Farms to be immersed in history, art, and nature.
- Tour Duration: Allow 2-3 hours to see the downtown area and visit Shelburne Museum/Farms.
- Top Attractions: Shelburne Museum, Shelburne Farms, Shelburne Vineyard
7
Stowe
View of Stowe Community Church during the fall, Vermont USA
Stowe is a charming Vermont town with a lot of things to do during the fall. It lies at the heart of this quintessential Vermont ski town surrounded by the stunning Green Mountains (which also offer superb glamping spots).
Historic Main Street offers locally-owned shops, art galleries, and restaurants within beautifully preserved 19th-century buildings. Walk along the picturesque Recreation Path riverwalk or relax on the Village Green. Nearby attractions include Stowe Mountain Resort, the Von Trapp Family Lodge, and the beautiful Stowe Community Church.
- Things to Do: Hike Mt. Mansfield, enjoy fall foliage, shop & dine downtown, and tour Von Trapp Lodge
- Top Attractions: Stowe Mountain Resort, Trapp Family Lodge, Vermont Ski & Snowboard Museum
6
Waitsfield
Waitsfield, Vermont, USA
Nestled in the heart of the scenic Mad River Valley, Waitsfield’s vibrant town center features a historic covered bridge and excellent dining, shopping, and lodging options.
Savour local fare at restaurants like American Flatbread and browse the fun shops along Bridge Street. Relax by the soothing Mad River walking paths or stop by the Big Picture Theater and Cafe, housed in a converted church. The nearby Mad River Glen ski area is a Vermont classic.
- Best Time to Visit: September-October for fall foliage and the Waitsfield Farmer’s Market Saturdays.
- Things to Do: Hike near Mad River Glen, shop and dine downtown, tubing down Mad River
5
Brattleboro
Brattleboro Co-op Building downtown, Vermont, USA
This artsy southern Vermont town centered around a lively pedestrian downtown set along the banks of the Connecticut River.
Stroll along historic Main Street and neighboring side streets with independent shops, cafes, and galleries. Catch a show at the renowned Latchis Theater or visit the Brattleboro Museum and Art Center—sample maple cree Latte’ at Mocha Joe’s famous coffee shop. The scenic River Walk and artsy galleries add to Brattleboro’s distinctive small-town culture.
- Hours: Most shops open daily, 10 am-5 pm, with venues like Latchis Theater open later for events.
- Top Attractions: Latchis Theatre, Brattleboro Museum & Art Center, Strolling of the Heifers festival.
4
Middlebury
Tour of Middlebury College, Vermont, USA
Home to Middlebury College, this charming Champlain Valley town offers an idyllic New England downtown centered around a picture-perfect village green.
Browse the shops and restaurants lining Main Street or stop at the Robert Frost Wayside Exhibit. Art lovers can visit the Henry Sheldon Museum of Vermont History or Middlebury College Museum of Art. Enjoy views of Otter Creek Falls, a stunning cascade in town, or the surrounding Green Mountains.
- Tour Duration: Allow 2-3 hours to stroll downtown and visit museums/galleries.
- Top Attractions: Middlebury College, Henry Sheldon Museum, Middlebury College Museum of Art.
3
Barre
The Robert Burns Memorial monument in downtown Barre, Vermont, USA
Vermont’s granite capital, Barre, offers one of the best downtowns in Vermont; it features unique architecture and sculpture throughout its historic downtown area.
See Hope Cemetery’s whimsical granite headstones or visit the Studio Place Arts Center in a converted granite warehouse. Look for the “Youth Triumphant” statue by Barre native Hiram Powers on the City Hall Lawn. Stop by the Granite Museum and explore downtown’s many granite-lined buildings and alleys showcasing the area’s mining heritage.
- Things to Do: View granite architecture, visit the Granite Museum, and see Hope Cemetery.
- Top Attractions: “Youth Triumphant” statue, Granite Museum, Studio Place Arts.
2
Woodstock
Downtown Woodstock, Vermont
Confusingly, when comparing Woodstock in New York and Woodstock in Vermont, travelers often get mixed up between the two. But the one in Vermont is definitely worth a visit. Sitting amid the pastoral countryside, Woodstock’s charming downtown invites leisurely strolling along historical Federal-style buildings surrounding a picturesque New England village green.
Quaint cafes, shops, bookstores, and galleries line the streets. Visit the impressive Marsh-Billings-Rockefeller National Historical Park or walk along the scenic Ottauquechee River. The nearby Suicide Six ski resort offers outdoor recreation in the soothing Vermont mountains.
Visitors can also enjoy vibrant art galleries, exquisite restaurants, and unique boutiques to dynamic markets in Woodstock.
- Best Time to Visit: September-October for Foliage and Harvest Festival. Sites like Marsh-Billings-Rockefeller close in winter.
- Top Attractions: Marsh-Billings-Rockefeller National Historic Park, Billings Farm & Museum.
1
Dorset
A historic building in Dorset Village, Vermont, USA
Listed on the National Register of Historic Places, Dorset’s quaint downtown is lined with Georgian, Federal, and Greek Revival architecture from the 18th and 19th centuries. The beautiful Dorset Green serves as a central village common surrounded by historic inns, the weekly farmer’s market, and the acclaimed Dorset Theatre Festival.
Nearby, the marble Dorset Quarry has drawn sculptors and artists to this southern Vermont town for centuries, imbuing it with a creative, cultured vibe.
- Hours: Dorset Playhouse shows and farmer’s market summer through fall. Many attractions closed in winter.
- Top Attractions: Dorset Quarry, Dorset Theatre Festival, Dorset Green.
