Discover Quaint, Charming New England in These Vermont Hamlets

These are the cutest, coolest towns in our state

It’s no secret that Vermont is home to beautiful landscapes and picturesque towns. The scenery and weather make it the ideal spot to get a taste of small-town life. In the summer, the weather is practically perfect; in the fall, the leaves change; in the winter, you can get cozy with a cup of hot cocoa or hit the slopes; in the spring, you can watch the flowers begin to bloom again. These are the best towns to visit in Vermont, at any point in the year.

Downtown Brattleboro / Facebook


This town – complete with an annual town meeting – is the beloved home to 12,000 people as well as the perfect spot for a getaway with family or friends. Industry is a large part of this town’s history, but the arts began to flourish here in the 70s. The town is made up of craftspeople, artists, musicians, farmers, bookshop owners, coffee aficionados, foodies, gallery owners, and ranchers. The bringing together of all different types of people provides a town in which you can enjoy wide-open spaces during your visit as well as good food, good coffee, good art, and good music. Each Saturday morning there is a farmer’s market filled with vendors and musicians.

Chester, VT Guide – Meet Chester, Vermont / Facebook


Originally a New Hampshire town, Chester became part of Vermont in 1761 making 2011 the 250th anniversary of the town. September would be an ideal time to visit as the weather is pretty much perfect and the Chester Fall Festival on the Green is hosted by the town every September. During your visit, the Stone Village Historic District and Chester Village Historic District are the places to be. They are both listed in the National Register of Historical Places, and include plenty of historic architecture as well as fun shops and restaurants.

Greensboro, VT / Doug Kerr / Flickr


Though less than 1,000 people live here all year, Greenboro’s lakeside cottages are busting at the seams in the summertime. This town has been a getaway for both Margaret Mead and Pulitzer-prize winner Wallace Stegner. While you’re visiting, go to the Highland Center for the Arts. The center has a 250-seat theater, small performance space, art gallery, and a café, making year-round performances, exhibits, and events like cinema workshops and lectures possible. Every summer, there is a youth circus arts program called Circus Smirkus. Other fun spots to visit during your stay include Willey’s Store, the Barr Hill Nature Preserve, and the Craftsbury Outdoor Center.

Grafton, Vermont / Facebook


Like most Vermont towns, Grafton offers plenty of natural beauty complemented by the charm of its main street and surrounding shops and homes. The historic Grafton Inn, open since 1800s, is in the center of the town. Presidents and famous philosophers have stayed here, and so can you! Many of the original buildings are upkept by the Windham Foundation. Interesting spots to check out include a small museum of local history, the Turner Hill Interpretive Center which tells the story of escaped slave Alec Turner and his family, the Nature Museum, the Fairy House trail, the Vermont Museum of Mining and Minerals, and the Grafton Trails and Outdoor Center.

Manchester Vermont / Facebook


Commonly a summertime respite for the wealthy, this town offers both luxury in its mansions and simplicity in its bed-and-breakfast inns. The son of Abraham Lincoln built a home overlooking the valley, and these days, it has a working farm, a goat cheese dairy, and a mansion that is open for tours. The home is fully furnished and has many pieces from Mary Todd Lincoln’s family. While in the town, you can also visit the American Museum of Fly Fishing, the Southern Vermont Arts Center, or climb Mount Equinox for a view of the town and mountain range.

Stowe Mountain Resort / Facebook


If you like skiing, you need to visit Stowe. This town is home to a world-class mountain resort. Though skiing is perhaps its best offering, Stowe is also home to year-round outdoor recreation, art, culture, and history. While visiting the town, you should see the Trapp Family Lodge, the Vermont Ski and Snowboard Museum, the Stowe Recreation Path, and the picturesque main street.


Take a seat on the porch of the Vermont Country store to look out on Weston’s main street and the town’s mill and water wheel. This country store draws people into Weston, but the charm of the town entices people to stay. This idyllic town is surrounded by plenty of natural beauty as well as shops and restaurants to entertain you. Visit the Vermont Scale Museum, the Farrar-Mansur House, and the Weston Playhouse Theatre during your stay.

Woodstock VT / Facebook


A model for land conservation and sustainable farming, Woodstock is a great place to live as well as to visit. One of Woodstock’s first citizens, George Perkins Marsh, is known as America’s first environmentalist. 70 years later, another Woodstock citizen Frederick Billings planted thousands of trees to eventually create Marsh-Billings-Rockefeller National Historic Park. This park is the only national park to focus on land stewardship. You can tour the grounds, a museum, the farm manager’s home, the barn, and the Rockefeller home. In town, you’ll find beautiful homes, a museum of local history, a beautiful covered bridge (a classic Vermont view), galleries, and boutiques. You can also go skiing in Woodstock at Suicide Six or the trails on Mount Tom.

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