The 10 Most Beautiful Towns in Vermont, USA

Windsor County’s town of Chester is best known for its Stone Village and Chester Village Historic Districts, both of which are listed in the National Register of Historic Places. Stone Village got its name for the predominance of granite houses, and the Chester Village features a typically New England Federal and colonial aesthetic. A popular tourist destination for its character, Chester is home to the Chester Fall Festival in September, charming inns, antique shops, galleries and great restaurants. Additionally, Chester offers opportunities for cyclists, boaters and snow skiers, lying in close proximity to Okemo, Mount Snow and Killington. For a quintessential Vermont experience, Chester provides a quiet and relaxing atmosphere.

The town of Dorset lies amid the hills of Bennington County in southern Vermont. Chartered in 1761, Dorset was the site of Cephas Kent’s famous tavern, which hosted meetings that eventually led to Vermont’s statehood. Dorset is also the location of America’s oldest marble quarry, which provided stone for the town’s sidewalks and the marble church next to the village green, as well as the main branch of the New York Public Library. A quiet and charming community in the highest valley between New York City and Montreal in Canada, Dorset has been a summer destination since the early 20th century, when artists and wealthy city-dwellers discovered the peaceful allure of the countryside. Take a swim in the quarry, partake in the Dorset Theatre Festival and explore the historical scenery for a relaxing and restorative mini-vacation.

Discover Grafton’s scenic beauty and historic buildings for a glimpse into America’s early colonial days. In the 1800s, Grafton was a popular stagecoach stop for those travelling to Albany, New York through the Green Mountains. As a result, the area acquired a market for hospitality, and maintains the Grafton Inn (formerly known as the Old Tavern), which dates back to 1801 and remains one of the oldest operating hotels in the United States. This picturesque village lies in the mountains of southern Vermont, and the residents have restored many of its original buildings to preserve its authentic New England atmosphere. Visitors can enjoy snow-covered hills and cross-country skiing, or wander the town’s array of shops and galleries.

A popular tourist destination for New Yorkers, New Englanders and even Europeans in recent years, Manchester is well known for its factory outlets and local businesses in the town center. Located in Bennington County, Manchester offers lots of recreational activities from shopping and dining to skiing and hiking. Manchester village has a vibrant cultural scene with museums, galleries, concerts and theatrical performances in addition to its natural and historical allure. Visitors can tour old buildings, peruse craft fairs and dine in one of many artisanal restaurants and cafés. Experience the best of authentic, old-world Vermont from covered bridges to rustic farmhouses in conjunction with the sophistication of a cultural town.

Montpelier may be the state capital of Vermont, but as the smallest state capital in the United States, it possesses all the charm and character of a small town or village. Since becoming the capital of Vermont in 1805, Montpelier’s primary focus has been in government. However, this small city offers a vibrant cultural scene with something for art-, music-, history- and nature-lovers alike. Visit the Vermont Historical Society Museum, the T.W. Wood Art Gallery and the Vermont State House, wander Hubbard Park and the Kellogg-Hubbard Library, and peruse farmers’ markets and quaint shops. As the site of the New England Culinary Institute, Montpelier also possesses a fantastic food culture with locally owned restaurants and cafés.

Located on the shores of scenic Lake Champlain, Shelburne is a lush and affluent suburb of Burlington, Vermont’s largest city. Shelburne has three main tourist attractions—the Shelburne Museum, Shelburne Farms and the Vermont Teddy Bear Company, in addition to a nature park and a beach on the lake with a boat launch. Roam the 19th-century Shelburne Farms estate, complete with a 110-room summer residence, five-storey barn and two-acre courtyard with hayrides, a walking trail and theatrical performances in the summer and autumn months. History buffs can enjoy learning about Vermont’s heritage at the Shelburne Museum, with a real lighthouse, steamboats, barns and a railway station, as well as daily demonstrations of printing, blacksmithing and weaving.

The lively town of Stowe is an ideal destination in all four seasons, but attracts a large number of visitors each winter to the highly popular Stowe Mountain Resort. The looming Mount Mansfield is the highest point in Vermont, perfect for visitors who enjoy skiing and snowboarding. In town, visitors can wander arts and crafts fairs, museums and galleries, attend musical and theatrical performances and partake in seasonal activities such as outdoor film festivals. Stowe is breathtakingly beautiful year-round, world famous for its vibrant fall foliage, rolling green hills in summer and cozy, snow-covered winters. Whether you’re an avid outdoors enthusiast or simply looking for a beautiful change of scenery, Stowe is one of Vermont’s most picturesque and beloved towns.

Located in the heart of the Mad River Valley in Washington County, Waitsfield is a popular destination for skiers who come to explore the area around Sugarbush Resort and Mad River Glen. As is common throughout the state of Vermont, Waitsfield is surrounded by stunning natural beauty, which has, in turn, attracted numerous talented artists and restaurateurs to set up shop in the town. Consequently, Waitsfield has a number of galleries and studios for tourists to visit, as well as movie theaters, live music venues and theatrical performances to attend. Those who love the outdoors can visit several farms, roam farmers’ markets and participate in nature-based recreational activities. With a rich heritage and broad selection of things to do, Waitsfield offers a relaxed yet lively atmosphere.

The small town of Weston, located in Windsor County, offers visitors an authentic, New England country experience. Weston is home to several charming bed and breakfasts, inns and lodges, perfect for a cozy romantic weekend or a fun family getaway. Visit quintessential country stores and shops selling Christmas ornaments, crafts and artisanal goods, galleries and craft studios—all of which are still family-owned and operated. Dine at welcoming restaurants and taverns to experience everything from relaxed bites to sophisticated meals. Weston is the perfect place for a quiet change of scenery in a picturesque town with a charming and well-preserved heritage.

The shire town and capital of Windsor County, Woodstock is one of Vermont’s most prized possessions. The town was settled in the mid 18th century, and continues to exude charm as the “quintessential New England village”, equipped with a centrally located covered bridge, a village green, restored Greek Revival, Federal and Georgian-style homes as well as old country farms and parks. Wander around the town center, sample maple syrups and cheeses at Sugarbush Farm and explore the Marsh-Billings-Rockefeller National Historical Park. Visit in the autumn to attend The Billings Farm and Museum’s annual Harvest Weekend, or simply enjoy the picturesque surroundings, beautiful year-round. For all the quaint colonial character of New England, Woodstock makes for the perfect weekend destination.