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Charming Quaint Towns in Vermont

By: Cityseeker
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Vermont is home to many beautiful small towns, each with its own unique charm. From picturesque villages to bustling downtowns, Vermont's small towns offer something for everyone. From outdoor activities to cultural attractions, these towns offer a variety of activities and experiences. Whether you're looking for a relaxing getaway or an adventure, Vermont's small towns have something for everyone.


Located in Vermont's Windsor County, Weston is a picturesque little town. Home to a number of vibrant shops with interesting local products, cozy restaurants and taverns that serve delicious breakfasts, local delicacies and cocktails, and quaint lodging options, Weston is a tranquil oasis to get away from the hustle and bustle of big cities. The Old Mill Museum, housed in a historic mill, brings the local history to life, while the famous Vermont Country Store is a fascinating place to shop for quirky souvenirs, body care products, and other exciting knickknacks.

Weston, Weston, VT, United States

Vermont's Chittenden County is home to Shelburne, a quaint little town that exudes an old-world, idyllic charm. Shelburne began as a small farming community that flourished with the advent of sawmills, gristmills, and shops. The Shelburne Museum brings its intriguing history to life through a variety of exhibits. The other two popular tourist attractions in the town are the Shelburne Farms, which is a bucolic working farm, and the Vermont Teddy Bear Factory, which is known to be one of the largest sellers of teddy bears in the world.

Shelburne, Shelburne, VT, United States

Surrounded by the snow-capped mountains of Vermont, Stowe is a perfect getaway during the colder months. Covered in an angelic-white carpet of snow, this little town is buzzing with visitors once winter sets foot. Stowe is defined by dramatic snow-dappled peaks and ski trails, characteristics that have earned it the epithet of being 'The Ski Capital of the East'. Ice skating, snowshoeing, dog sledding, ice-fishing, and snowmobiling, are other activities that Stowe is famous for, making the town a treat for outdoor enthusiasts. It is famously home to the Stowe Mountain Resort, which is popular for its skiing facilities along with other winter sports. Other attractions include the Vermont Ski and Snowboard Museum, Smugglers' Notch State Park, and Mount Mansfield.

Stowe, Stowe, VT, United States

Tucked away in the lush mountains in Vernon's Windham County, Grafton offers a serene getaway from busy urban life. Known to be one of the most picturesque villages of New England, this little unassuming town is big on unique experiences. With its history dating back to the 19th Century when it flourished as a stagecoach hub, Grafton is dotted with archaic structures that narrate intriguing stories of its past, along with newer shops, restaurants, galleries, museums, and accommodations. The Nature Museum is one such interesting attraction that is a treat for the little ones. Other attractions include the Grafton Trails & Outdoor Center and Plummer's Sugar House.

Grafton, Grafton, VT, United States

This charming historic town is nestled in the lap of mountains in Vermont's Bennington County. A stunning visual treat, Dorset is an ideal destination throughout the year. Steeped in history and interesting anecdotes of its past, the sleepy town is also an ideal location to become one with nature and enjoy a variety of outdoor activities like hiking, mountain biking, golfing, fishing, and more. The Emerald Lake State Park is one such beautiful outdoor attraction, which is home to the crystal-clear Emerald Lake. History buffs can revel in its old-world charm and explore fascinating attractions like The Dorset Historical Society Bley House Museum.

Dorset, Dorset, VT, United States

Woodstock is a charming village tucked away in Vermont's Windsor County. A mélange of lively annual events, delicious dining options, cozy bed and breakfasts, exciting entertainment venues and more, Woodstock invites many visitors every year with its pleasant, quaint charm. The Billings Farm & Museum, with its bucolic atmosphere, makes for a delightful treat. The Marsh-Billings-Rockefeller National Historical Park is another popular attraction that features lush green gardens and verdant environs. The Sugarbush Farm is another rustic spot where visitors can sample varieties of cheese and buy authentic local products.

Woodstock, Woodstock, VT, United States

Located in Vermont's Windsor County, Chester is a charming little town that exudes a quaint yet lively vibe. Home to the Chester Village Historic District and the Stone Village Historic District, the town is steeped in intriguing history. The rustic streets are flanked by old structures that exemplify Colonial, Victorian and Federal styles of architecture, many of which are listed on the National Register of Historic Places. Every year, Chester also hosts the Chester Fall Festival and the Winter Carnival.

Chester, Chester, VT, United States

Manchester is a charming town tucked away amid the Green Mountains in Vermont's Bennington County. A popular tourist town, Manchester attracts hordes of visitors every year thanks to its pleasant charm and atmosphere. Dotted with cozy inns and cottages, vibrant eateries, quirky shops and much more, the town offers an array of fun experiences. The American Museum of Fly Fishing is a treat among history buffs and anglers alike, with its unique exhibits. For art and culture buffs, the Southern Vermont Arts Center is a splendid attraction. Outdoor attractions in the town include the Equinox Mountain and Lye Brook Falls.

Manchester, Manchester, VT, United States

Waitsfield is a picturesque town located in Vermont's Washington County. Primarily a small agrarian community, Waitsfield's landscape is defined by charming cottages, verdant woods, and historic buildings. Offering dramatic views of the Mad River Valley, the town attracts many tourists every year who come looking for its quaint, rustic atmosphere coupled with exciting opportunities for outdoor activities like hiking and winter sports. For art and history buffs, Waitsfield is home to attractions like the Bundy Modern and Waitsfield Covered Bridge.

Waitsfield, Waitsfield, VT, United States, 05673

Tracing its origins way back to 1781, Montpelier is presently the capital of Vermont and the smallest state capital because of its small population. Finally incorporated in 1818, it became a pivotal trading city with impressive manufacturing units, power mills, iron foundries, quarries, furniture, clothes, and more. The city did not lose its strategic importance through the centuries, which explains why it still is the state capital. Montpelier boasts a number of art centers, museums, galleries, cafes, bars, and touristy attractions for visitors. Some notable attractions include the Vermont History Museum, Hubbard Park, and the Vermont State House.

Montpelier, Montpelier, VT, United States, 5601

Bennington is a picturesque town in Vermont's Bennington County. One of the largest towns of Vermont, Bennington became known for the Battle of Bennington in the 18th Century. Today, the towering obelisk of Bennington Battle Monument commemorates the battle. Visitors can explore the town's intriguing bygone era at the Bennington Museum, which is home to an impressive collection of artifacts. Another important landmark of the town is the "Old First" Congregational Church. Bennington also hosts a number of annual events such as The St. Patrick's Day Parade, Fallapalooza, and Mayfest in May.

Bennington, Bennington, VT, United States

Middlebury is the seat of Vermont's Addison County. Chartered in 1761, Middlebury is now home to the Middlebury College. A melange of art and culture, the town has a variety of experiences to offer. It houses the oldest community museum in the country, the fascinating Henry Sheldon Museum, which features an impressive collection of historical exhibits. The Vermont Folklife Center is another educational attraction that features documentary exhibits. For outdoor enthusiasts, the town offers the picturesque Trail Around Middlebury and the 18-hole Ralph Myhre Golf Course.

Middlebury, Middlebury, VT, United States
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