Montpelier, Vermont, USA Town Skyline in Autumn.

Vermont's Best Small Towns for a Weekend Escape

Vermont, known for its scenic beauty, quaint villages, and welcoming hospitality, is a haven for charming small towns. The state is home to a variety of picturesque locales, each offering unique attractions, from historic landmarks to stunning natural vistas. This article showcases nine of Vermont's best small towns, highlighting their key attractions, including rivers, lakes, parks, and local businesses. From the vibrant arts scene of Brattleboro to the scenic shores of Shelburne, each town offers something special for visitors seeking a delightful weekend escape.

Woodstock

Early Autumn Foliage Scene of Houses in Woodstock, Vermont Mountains.
Early Autumn Foliage Scene of Houses in Woodstock, Vermont Mountains.

In the heart of Vermont, Woodstock is a picturesque town known for its charming historic district and vibrant arts scene. The Marsh-Billings-Rockefeller National Historical Park offers beautiful trails and stunning vistas. Billings Farm & Museum showcases Vermont's rural heritage, offering interactive exhibits and a working dairy farm experience. The town's vibrant downtown area is filled with boutique shops, art galleries, and delightful restaurants that showcase local flavors and artisanship. The Woodstock Inn & Resort provides elegant accommodations with top-notch amenities, including a luxurious spa and a golf course.

In the winter, Woodstock transforms into a winter wonderland, perfect for skiing and snowshoeing, while in the summer, the town is alive with outdoor festivals, farmers' markets, and concerts on the green. The Ottauquechee River, which flows through the town, offers opportunities for kayaking, fishing, and scenic river walks. Woodstock's scenic riverfront, rich history, and welcoming community make it a gem in southern Vermont.

Stowe

Panoramic Aerial View of Stowe, Vermont in Fall.
Panoramic Aerial View of Stowe, Vermont in Fall.

Stowe, often referred to as "the Ski Capital of the East," is a delightful town offering a variety of outdoor activities. The Stowe Mountain Resort provides luxurious accommodations and easy access to the slopes, making it a popular destination for skiing and snowboarding in the winter. The scenic Stowe Recreation Path is perfect for walking or biking, offering stunning views of the surrounding mountains and meandering along the West Branch River. Mount Mansfield, Vermont’s highest peak, offers breathtaking views and hiking trails, perfect for outdoor enthusiasts.

Stowe’s charming Main Street is home to a delightful array of shops, restaurants, and cafes, offering everything from local crafts to gourmet dining. The town's vibrant arts scene is highlighted by the Vermont Ski and Snowboard Museum, which offers a fascinating look at the state's winter sports history. For nature lovers, Smugglers' Notch State Park provides beautiful trails and scenic overlooks, making it a perfect destination for hiking and wildlife spotting.

In the summer, Stowe transforms into a paradise for outdoor activities, including mountain biking, zip-lining, and golfing. The town also hosts various events and festivals throughout the year, including the popular Stowe Winter Carnival and the Vermont Pumpkin Chuckin' Festival. With its picturesque landscapes, vibrant downtown, and abundance of outdoor adventures, Stowe is a must-visit destination in Vermont.

Manchester

Lincoln Family Home, Former Summer Residence of Robert Todd Lincoln, Manchester, Vermont, USA.
Former Summer Residence of Robert Todd Lincoln, Manchester, Vermont, USA. Editorial credit: Jay Yuan / Shutterstock.com

Manchester is a quaint town known for its upscale shopping, historical sites, and outdoor adventures. The Equinox Golf Resort & Spa offers luxurious accommodations and amenities, including a world-class golf course and a relaxing spa. Visitors can explore Hildene, the Lincoln Family Home, which offers a glimpse into the life of President Lincoln's son Robert and features stunning gardens and panoramic views of the Battenkill River Valley. The town's charming Main Street is lined with unique boutiques, antique shops, restaurants, and cafes, offering something for everyone.

Outdoor enthusiasts will enjoy the Equinox Preservation Trust, which features scenic trails, pristine streams, and stunning views of Mount Equinox. The nearby Lye Brook Falls Trail offers a picturesque hike to one of Vermont’s highest waterfalls, while the Battenkill River provides opportunities for kayaking, tubing, and fly fishing.

In the winter, Manchester is a popular destination for skiing and snowshoeing, with Bromley Mountain and Stratton Mountain just a short drive away. The town also hosts various cultural events and festivals throughout the year, including the Manchester Music Festival and the Vermont Summer Festival. With its blend of historic charm, cultural attractions, and natural beauty, Manchester is a standout destination in southern Vermont.

Middlebury

Two chairs overlooking a scene of Vermont foliage at Middlebury College.
Two chairs overlooking a scene of Vermont foliage at Middlebury College.

Middlebury is a vibrant college town with a rich history and cultural scene. The Inn on the Green offers cozy accommodations in the heart of downtown, making it an ideal base for exploring the town's attractions. The beautiful Middlebury College campus is home to the Middlebury College Museum of Art, which features an impressive collection of American and European art. The town's vibrant downtown area is filled with boutique shops, restaurants, and cafes, offering a charming and lively atmosphere.

Nature lovers will enjoy Otter Creek, which flows through the town and provides opportunities for kayaking, fishing, and scenic river walks. The Henry Sheldon Museum of Vermont History offers a fascinating glimpse into the town's past, while the Middlebury Town Green hosts various community events and concerts throughout the year.

For outdoor enthusiasts, the nearby Robert Frost Interpretive Trail offers a peaceful hike through the Vermont countryside, while the Middlebury Snow Bowl provides skiing and snowboarding in the winter. The town is also home to several charming covered bridges, including the Pulp Mill Covered Bridge and the Halpin Covered Bridge, which add to the town's picturesque charm. With its mix of cultural attractions, natural beauty, and vibrant community, Middlebury is a true gem in the heart of Vermont.

Brattleboro

Aerial View of Brattleboro, Vermont, USA, in Spring on a Partly Cloudy Day.
Aerial View of Brattleboro, Vermont, USA, in Spring on a Partly Cloudy Day. Editorial credit: SEALANDSKYPHOTO / Shutterstock.com

Brattleboro is a vibrant town known for its artsy vibe and scenic riverfront setting. The Latchis Hotel and Theatre offers unique accommodations in a historic Art Deco building, providing a perfect base for exploring the town's eclectic shops, galleries, and restaurants. The West River Trail offers scenic hiking and biking opportunities along the river, while Fort Dummer State Park provides a peaceful setting for camping, hiking, and picnicking.

The town's vibrant arts scene is highlighted by the Brattleboro Museum & Art Center, which features rotating exhibits of contemporary art and hosts various events throughout the year. The Latchis Theatre, located within the hotel, is a stunning Art Deco cinema that showcases movies, live performances, and cultural events.

For nature lovers, the nearby Wantastiquet Mountain offers a challenging hike with rewarding views of the Connecticut River Valley, while the Retreat Trails provide a network of scenic trails through the woods and along the river. The town also hosts various festivals and events throughout the year, including the Brattleboro Literary Festival and the Strolling of the Heifers Parade. With its vibrant arts scene, beautiful riverfront, and welcoming community, Brattleboro is a unique and inviting destination in southern Vermont.

Grafton

Grafton Village Historic District.
Grafton Village Historic District. By Samturgeon, CC BY-SA 3.0, Wikimedia Commons

Grafton is a picturesque village that feels like stepping back in time. The Grafton Inn, one of the oldest operating inns in America, offers charming accommodations and a taste of New England history. The town's historic buildings, covered bridge, and tree-lined streets create a storybook atmosphere, perfect for a relaxing weekend escape.

The nearby Grafton Trails & Outdoor Center offers hiking, biking, and skiing in a beautiful natural setting, while the Grafton Village Cheese Company allows visitors to sample delicious Vermont cheeses and learn about the town's cheese-making tradition. The town's small size and peaceful surroundings make it an ideal destination for those seeking a tranquil retreat in the Vermont countryside.

Grafton is also home to several charming shops, galleries, and restaurants, offering a delightful blend of local crafts, art, and cuisine. The Grafton Historical Society Museum provides a fascinating look at the town's past, while the Grafton Ponds Outdoor Center offers year-round activities, including snowshoeing, cross-country skiing, and mountain biking.

In the fall, the town is a popular destination for leaf-peepers, with its vibrant foliage and scenic countryside. With its combination of historic charm, natural beauty, and welcoming community, Grafton is a truly special destination in Vermont.

Shelburne

View of Lake Champlain and Adirondack Mountains from Shelburne Farms, Vermont.
View of Lake Champlain and Adirondack Mountains from Shelburne Farms, Vermont.

Shelburne is a charming town located on the shores of Lake Champlain. The Inn at Shelburne Farms offers luxurious accommodations on a historic estate, providing stunning views of the lake and the surrounding mountains. The town is home to the Shelburne Museum, which features an impressive collection of American folk art and historic buildings, as well as beautiful gardens and scenic walking paths.

The Shelburne Bay Park Trail offers a scenic walk along the lake, with beautiful views of the water and the Adirondack Mountains in the distance. The town's charming village center is home to unique shops, restaurants, and cafes, offering a delightful blend of local flavors and crafts.

For outdoor enthusiasts, the Shelburne Pond Natural Area provides opportunities for hiking, birdwatching, and fishing, while the Shelburne Farms offers educational tours and activities for visitors of all ages. The town is also home to several wineries and breweries, offering tastings and tours of Vermont's local beverages.

In the summer, the town hosts various events and festivals, including the Vermont Mozart Festival and the Shelburne Vineyard Harvest Festival. With its beautiful lakeside setting, vibrant cultural scene, and welcoming community, Shelburne is a must-visit destination in Vermont.

Waitsfield

Aerial View of Waitsfield, Vermont, and the Mad River on Scenic Route 100 in Autumn.
Aerial View of Waitsfield, Vermont, and the Mad River on Scenic Route 100 in Autumn.

Waitsfield is a charming town in the Mad River Valley, known for its scenic beauty and outdoor adventures. The Pitcher Inn offers luxurious accommodations with rustic charm, making it a perfect base for exploring the town's attractions. The Mad River Path offers scenic hiking and biking trails along the river, while the historic Waitsfield Covered Bridge is one of Vermont's oldest and most picturesque covered bridges. The town's charming village center features unique shops, restaurants, and galleries, providing a delightful blend of local art and cuisine.

Outdoor enthusiasts can enjoy skiing and snowboarding at the nearby Sugarbush Resort, one of Vermont’s largest ski areas, or explore the beautiful trails of the Mad River Glen Ski Area, which offers some of the best skiing in New England. In the summer, Waitsfield comes alive with farmers' markets, outdoor concerts, and various festivals, including the Vermont Festival of the Arts and the Waitsfield Common Festival.

The town's picturesque setting in the Green Mountains provides ample hiking, fishing, and kayaking opportunities, while the nearby Mad River offers scenic views and refreshing swimming holes. With its blend of natural beauty, cultural attractions, and welcoming community, Waitsfield is a true gem in the heart of Vermont.

Montpelier

Autumn Town Skyline of Montpelier, Vermont, USA.
Autumn Town Skyline of Montpelier, Vermont, USA.

Montpelier, the capital of Vermont, is a small town with a big personality. The Capitol Plaza Hotel & Conference Center offers elegant accommodations in the heart of the city, providing a perfect base for exploring Montpelier's attractions. Visitors can explore the Vermont State House, one of the oldest and best-preserved capitols in the country, or take a walk along the scenic North Branch River Park Trail, which offers beautiful views of the city and the surrounding mountains.

The town's vibrant arts scene is highlighted by the Lost Nation Theater, which hosts various performances and events throughout the year, as well as the Vermont College of Fine Arts, which offers a variety of art exhibitions and workshops. Hubbard Park provides a beautiful setting for hiking, picnicking, and wildlife watching, while downtown Montpelier is home to charming shops, cafes, and restaurants, offering a delightful blend of local flavors and crafts.

For outdoor enthusiasts, the nearby Camel's Hump State Park offers challenging hikes and stunning vistas, while the North Branch Nature Center provides opportunities for birdwatching and nature exploration. The town also hosts various festivals and events throughout the year, including the Green Mountain Film Festival and the Montpelier Arts Walk. With its blend of cultural attractions, natural beauty, and welcoming community, Montpelier is a unique and inviting destination in Vermont.

Explore the Quintessential Charm of Vermont's Small Towns

In conclusion, Vermont's small towns offer a delightful mix of natural beauty, history, and vibrant culture, making them perfect for a weekend escape. From the charming streets of Woodstock to the scenic shores of Shelburne, these destinations showcase the best of what Vermont has to offer. Whether you are seeking outdoor adventures, cultural experiences, or a relaxing getaway, these nine towns provide the perfect setting for an unforgettable Vermont vacation.

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