10 Must-Visit Small Towns in Vermont

Chester is a charming small town in southern Vermont that’s ideal for outdoor adventures in any season. Located on the slopes of the Green Mountains, Chester is fun for winter sports and warm-weather activities like hiking, biking, and mountain climbing.

You’ll find plenty of historic sites in Chester, such as the Stone Village Historic District and the Chester Factory Village, which boasts Victorian, colonial revival and federal style buildings. Chester also has many art galleries, quaint antique shops, and artisan shops, so you can bring home some unique gifts from your visit.

Dorset, with its quintessential New England charm, is a vibrant destination for arts and culture and outdoor fun in all seasons. Many people flock to Dorset for winter fun at the nearby Bromley Mountain and shopping in Manchester, but there’s a lot more to do.

During warm weather, the Emerald Lake State Park provides a recreational lake and tour operators for boating, fishing, and beach days, and you can hike, ski, climb, or snowboard on Dorset Mountain all year long.

Grafton is a beautiful alpine village located in the mountains of southern Vermont, with stunning historic buildings, galleries, museums, and independent shops. You’ll find many fascinating museums in Grafton, such as the Nature Museum and the Vermont Museums of Mining & Minerals.

You could also visit the Grafton Historical Society to learn about the historic sites in the area and take a tour. If you like the outdoors, spend some time at the John Grafton State Park to explore the woodlands and wetlands.

Manchester is the place to go in Vermont if sightseeing is up high on your list of things to do. The town is home to fascinating points of interest like Hildene, which is the estate of Abraham Lincoln’s son Robert, and the American Museum of Fly Fishing, which is home to artwork and artifacts of fly-fishing heritage.

If you like art, you can see a sculpture garden and a variety of exhibits at the Southern Vermont Arts Center. For fun in the outdoors, take the woodland trails to Mount Equinox for some spectacular landscape views.

Montpelier is Vermont’s capital and a charming small town for a retreat, known for its food, maple syrup farms, and historic sites. You’ll find a variety of maple syrup attractions, such as sugarhouses, farms, maple creameries, and a farm-life museum, as well as tasting tours.

Montpelier also has a lot of cultural attractions, such as concerts and stage performances at the Lost Nation Theater. For historic interest, take a walking tour of the downtown area to see the Vermont Historical Society Museum and the State House with its statue of Ethan Allen, the Revolutionary War hero.

Shelburne is a suburb of Burlington and an excellent place for a retreat. The town has a lot of fun of its own, such as adventures on Lake Champlain and shopping and dining in town. One of the highlights is the Shelburne Museum, where you'll find a fascinating collection of art, design, and Americana.

If you stay near the museum, you can visit to see over 150,000 works in over a dozen historic buildings spanning 45 acres. Also check out Shelburne Farms, which is a quaint farm with animals and educational programs for the kids.

Stowe is a popular destination at the foot of Mount Mansfield for winter sports and outdoor recreation. The town boasts many ski trails and slopes, as well as the Vermont Ski and Snowboard Museum.

In warm weather, you can visit Smugglers’ Notch State Park to hike in the forest and take the trails through the mountain pass. You can also hike to scenic hidden falls, such as Bingham Falls and Moss Glen Falls, for spectacular scenery and photo opportunities. You can swim at the base of the falls in warmer months.

Waitsfield is a picturesque small town that offers beautiful landscapes and excellent opportunities for outdoor recreation. You can ski or snowboard at Mad River ski resort or spend your time on hiking and biking trails in Scrag Mountain Town Forest.

The area offers plenty for history and culture enthusiasts as well, such as the Madsonian Museum of Industrial Design and historic covered bridges. During your trip, be sure to visit Hartshorn’s Organic Farm Stand and Maple Sugar House to sample the goods.

Weston is a town nestled in the Green Mountains that’s known for its historic charm and scenic beauty. You can find a diverse mix of things to see and do in Weston, from visiting period homes and shopping in charming antique shops to spending your time exploring the ski slopes and forests.

The downtown area is one of the top spots, boasting quaint general stores, local museums, delicious eateries and cafés, and no shortage of unique shopping opportunities, especially during the holiday season.

Woodstock is a town that boasts a rich history and intriguing attractions for a memorable sightseeing trip in Vermont. Historic buildings can be found just about anywhere you look, especially near the central square. You can visit places like the Norman Williams Public Library, the Billings Farm & Museum dairy farm, and the Calvin Coolidge Historic Site.

Consider visiting the Marsh-Billings-Rockefeller National Historical Park, which features a 19th-century Queen Anne-style mansion on a vast green space filled with hiking trails. Foodies will love visiting the Quechee Gorge Village, a quaint village with cheese shops that offer the finest Vermont cheeses.