7 Whimsical Towns to Visit in Vermont

Favorite Vermont resident Robert Frost wrote, "Two roads diverged, and I took the one less traveled by, and that has made all the difference." Perhaps he was talking about these whimsical small towns. The ones that may not be as well known as others in New England yet possess a magical appeal. The Green Mountain State has a variety of storybook communities dotted around the landscape. Pumpkin festivals in Bennington and unique antiques in Hartford are just a few reasons those in the know keep coming back year after year. Read on to discover why these fanciful enclaves should be next on your must-see lists.

Bennington

Awash with charm, this town is home to Revolutionary War landmarks and New England heritage. The centerpiece of this town is the 1889 monument for the Battle of Bennington. Around 300 feet high, it is the tallest structure in the state. Bennington comes alive in the fall with whimsical pumpkin and apple festivals. Set in historic downtown, over 500,000 visitors participate in two months of harvest events, including parades, bake-offs, and costume re-enactments.

Technicolor statues are installed throughout the historic district. Now listed on the National Registry, walking tours take you past 18th and 19th architectural masterpieces. Specialty shops line main streets, selling vintage furniture and locally sourced treats. Stroll along the maple tree-lined streets near Bennington College to the Robert Frost Museum and the adorable Dollhouse and Toy Museum of Vermont.

Weston

Initially a sawmill and stone cutters industry, it now attracts tourism for two of its highest-profile businesses. The state's oldest continuously running theatre company, The Weston Theatre Company, was founded in 1935.

You might remember your grandparents getting a catalog from the Vermont Country Store. In operation since 1946, this red clapboard general store is a step back in time. Selling everything from medicinal potions to old-fashioned candy, it is authentic Vermont at its best. A short walk from the store will take you to the Mill Museum, housed in an original 18th-century mill. Learn everything you never thought you needed to know about our forefathers' most extensive commerce. Set along the riverbanks, it is ideal for a picnic lunch.

Shelburne

Nestled on the banks of Lake Champlain, this farming town was founded in the late 18th century, later focusing on shipbuilding. The round design of the Shelburne Museum is reason enough to visit. Don't be fooled by this whimsical structure; however, inside is a collection of original paintings by Degas and Rembrandt. An open-air amphitheater welcomes musicians throughout the year, and people of all ages can take classes in various art mediums.

Orchards and vineyards are plentiful in this close-knit community. Shelburne Farms, a National Historic Landmark, is the oldest working farm in the state. Offering lessons on organic agriculture and seeding, this non-profit has remained in the same family since the 1800s.

Woodstock

If it feels like almost every corner of this town has its stamp on American history, it's because it has. Established from a land grant for the Duke of Marlborough, its name derives from its territory in Oxfordshire, England. Revolutionary and Industrialist history abounds here. Home to some of the country's most esteemed families of the 18th and 19th centuries, including the Rockefellers, its position as an architectural feast for the eyes is cemented.

This town was meant for walking; begin your day with a stroll around the town Green, and take that perfect Instagram reel at the covered bridge. Next, head to Historic Park and marvel at the farmhouse and colonial design. The Woodstock Historical Society is housed in an 18th-century building, with enthusiastic volunteers ready to share their best stories about some of the quirky heritage of Woodstock. Gillingham, Woodstock's oldest store, is a perfect blend of authentic Vermont with contemporary twists. End your day at the Long Trail Brewery and sample local house ales while enjoying the panoramic views of the Ottaquechee River.

Montpelier

The smallest state capital in the USA, Montpelier, founded in 1787, was recently voted one of USA Today's 10 Best Towns in the Northeast for 2024. It is rich in American history and one of the first incorporated towns by our founding fathers. A covered bridge oasis, you have your share to choose from. One of the best experiences occurred during the fall at Coburn Covered Bridge. A popular site for engagements, local lore promises that if you cross it with your special someone, you will be together forever.

Independently operated specialty boutiques are one reason Montpelier is continually among America's best small-town shopping destinations. You can find everything from homemade soaps to hand-hammered copper pots along Main Street. If you are craving a maple latte, it will be a locally-owned cafe you will support; there are no chains in Montpelier. To truly immerse yourself in Vermont life, Morse Farm Maple Sugarworks is the place to go. Less than three miles outside the city center, guests can walk the Maple trail, learn how to tap trees, and say hello to Rex and James, the farm's unofficial mascots.

Stowe

Well known for its snow activities, Stowe has been a popular destination for the last fifty years. But don't just limit yourself to visiting in the winter. This charming hamlet is full of whimsy all year round. Take the gondola ride up to Mount Mansfield for stunning views of the fall foliage or in the spring when Stowe is blanketed with wildflowers. Navigate through 300 acres of farmland featuring intricately designed corn mazes at nearby Sam Mazza's.

The Ben and Jerry's factory tour is twenty minutes away in nearby Waterbury. Sample over 40 flavors of Vermont Creamery ice cream and create your own bespoke flavor. Try locally brewed ale at the whimsically decorated Alchemist Brewery.

Hartford

Antiquing reigns supreme in Hartford, so much so that each year, the town hosts a community-wide flea market where residents can set up booths. It attracts vintage hunters from all over the East Coast. The Vermont Antique Market is a year-round showroom that sells furniture, housewares, and even contemporary gifts like Maple leaf-style jewelry.

Enjoy the outdoors at Quechee Gorge. Navigate the scenic trails to waterfalls and panoramic views. The Vermont Institute of Science houses many species of birds. This sanctuary allows guests to interact one-on-one or simply enjoy the beautiful space. Take a walking tour around the covered bridges. Taftsville and Quechee are two of the most historic in the state. End your day with dinner at Simon Pearce; continental cuisine in an 19th century mill with scenic views of waterfalls.

Like the saying goes, good things come in small packages and Vermont is the ideal place to test that theory. Contemporary lifestyle on colonial foundations combine to create the perfect holiday. Whether it's outdoor explorations or unique experiences these towns provide irreplaceable memories.