2024's 7 Most Adorable Small Towns in Vermont

Vermont, one of the New England states, is small both in population (49th of 50) and land area (45th). Yet the “Green Mountain State” packs plenty of natural beauty and small-town charm into a small package! Without any big cities, Vermont truly is a place defined by its small towns, which are full of history and populated by welcoming and proud locals. Among Vermont’s dozens of postcard-pretty small towns, check out our list of seven of the most adorable.

Brattleboro

Brattleboro is a popular day-trip destination for visitors from Vermont as well as New Hampshire, which is just across the Connecticut River, and Massachusetts, which is only a few miles away. This community of 12,000 has a classic downtown area, lined with red-brick buildings housing a nice range of shops and eateries. Your walking tour also has to include Brattleboro’s Municipal Center, housed in the Gothic-style former high school. Visit in summer to enjoy great kayaking on the river, or come in wintertime to hit the ski slopes on nearby Mount Snow. If you enjoy quirky musical instrument museums, check out the Estey Organ Museum.

Grafton

From its spot in the Green Mountains, Grafton has been an important stagecoach stop, a soapstone mining center, and a home to textile mills along the Saxtons River. Several historic buildings, most notably the 1801 Grafton Inn, have witnessed Grafton’s past and now serve its present as a tourist destination. This town of only 600 also has two great museums, the Grafton Historical Society Museum, and the Grafton Nature Museum. Be sure to take a photo at the classic McWilliam Covered Bridge, then sample the wares of the nearby Grafton Village Cheese Company.

Manchester

Manchester has become a popular regional shopping destination because of the Manchester Designer Outlets, but you will enjoy visiting the town even if you are not looking for name-brand deals. The downtown area offers local boutique shopping and three historic districts, and Manchester’s architectural highlights include the 1905 Hildene House, a luxurious former summer home with fantastic gardens. If you prefer a bigger challenge than a garden stroll, try hiking the trails up Mount Equinox to enjoy stunning views of the Green Mountains to the East and the Taconic Mountains to the West.

Montpelier

Montpelier, with only about 8,000 residents, is the smallest state capital in the nation, giving it a unique combination of small-town charm and capital-city amenities. The Vermont State House, Vermont History Museum, and other state-affiliated institutions give visitors plenty to explore, yet you can also enjoy a quiet stroll down Montpelier’s quaint State Street business corridor. Surprisingly enough, though, many locals think the best walking spot in Montpelier is Green Mount Cemetery, which pairs ornate funerary architecture with lush rolling hills. The Winooski River, which unfortunately causes occasional flooding issues, also offers opportunities for boating and kayaking.

Shelburne

The town of Shelburne might occupy the ideal location in Vermont—alongside Lake Champlain, fewer than ten miles from Burlington, and within sight of the Adirondack Mountains to the west and the Green Mountains to the east. No matter the time of year, but most especially when the fall colors are at their peak, Shelburne is perfect for a nature walk along the glistening lakeshore. Shelburne also has a nice collection of visitor attractions, including the Shelburne Museum (home to the steamboat SS Ticonderoga), the Vermont Teddy Bear Company factory, and Shelburne Farms (a sustainable agriculture educational nonprofit).

Stowe

Skiers know Stowe, home to Stowe Mountain Resort, as one of the premier ski spots in the eastern United States. Meanwhile, lovers of classic films may recognize Stowe as home to the Trapp Family Lodge, founded by the singing von Trapp family of Sound of Music fame in the 1940s. Artists also have an affection for Stowe, which is a haven for painters and home to renowned galleries like the Helen Day Art Center and Northwood Gallery. And, if you still have not found a reason to visit, Stowe has a picture-perfect New England downtown and is considered one of the best fall foliage viewing areas in the region!

Woodstock

In the era before electricity, the town of Woodstock grew wealthy by harnessing the flow of the Ottauquechee River to power numerous wool and textile mills. While the mills have long since shuttered, several of the finest homes from that era were preserved, with some now serving as charming bed-and-breakfasts. Woodstock still looks and feels like a classic New England town, with a covered bridge, a weekly farmer’s market, and a “town crier” message board in the heart of downtown. This town of 3,000 also hosts several fun community events, including the annual Harvest Weekend in October and Wassail Weekend each December.

Plan Your Vermont Adventure Today!

Vermonters are overwhelmingly proud of their unique little state, including its many classic small towns. While famous for their independent spirit, nearly all the residents of these communities are also extremely welcoming to visitors who want to experience small-town life in the Green Mountain State. So do not delay in making your 2024 Vermont travel plans—no matter the time of year, you will have a fantastic experience exploring its adorable small towns!