8 Quirkiest Vermont Towns You Didn't Know Existed
Vermont is a majestic state where a number of quirky small towns thrive within massive mountains. The state’s name (derived from the French “les monts verts” or “green mountains”) alludes to the alluring Green Mountains that dominate the landscape, and tucked within these mountainous realms are some eccentric Vermont towns you may not know exist, such as Stowe and Woodstock, with their cultural relevance. These destinations promise not only incredible backdrops but also a chance to connect with the heart and soul of New England living. You will have a fun and merry experience in some of the quirkiest Vermont towns you did not know existed.
Stowe
Stowed within the shadow of Vermont’s highest peak, Mount Mansfield, the mountainous town of Stowe is a quirky and charming destination known popularly as the “Ski Capital of the East." It is here that travelers can entertain themselves with numerous world-class resorts, snow-covered slopes, and family-friendly recreation areas like Smugglers’ Notch State Park for many thrills and exhilarations. The Auto Toll Road, on the other hand, is a route filled with spectacular panoramic views as it winds up Mount Mansfield. Those eager to learn more about the culture and etiquette of Stowe can enter the Vermont Ski and Snowboard Museum, which showcases vintage gear and local legends of the sport.
Summer brings a different kind of magic with the Music in the Meadow concerts filling the landscape with jazz and classical performances from July to August. Come autumn in October, Stowe hosts the quirky Vermont Pumpkin Chuckin’ Festival and the lively Von Trapp Brewing Oktoberfest. Whether you are relaxing at the riverside or enjoying luxury at the Trapp Family Lodge, which is run by the descendants of the real von Trapp family, Stowe is a captivating destination for every season.
Woodstock
Woodstock is a timeless New England village with many quirks and offbeat wonders to behold. At the heart of the town is the Green, a bucolic and rejuvenating central square lined with historic buildings, including the pink-hued Norman Williams Public Library, dating back to 1883.
Just outside town, the Billings Farm & Museum presents a hands-on glimpse into Vermont’s agrarian roots, showcasing life on a working dairy farm from the 19th century. History can be appreciated further at the Marsh-Billings-Rockefeller National Historical Park, where visitors can tour a grand Queen Anne mansion and walk through old-growth forests once protected by the nation’s early conservationists.
Summertime events, such as those run by Artistree, fill Woodstock’s streets with many musical performances in June. Those more interested in leisurely walks and strolls can hike up Mount Tom or kayak on Silver Lake. Finally, for those seeking to stay long in Woodstock, consider booking a room at refined accommodations such as the Woodstock Inn & Resort, the Woodstocker B&B, or The Shire Woodstock.
Montpelier
Montpelier, though Vermont’s capital city, feels more like a cozy village than a bustling metropolis. With fewer than 8,000 residents, it is the smallest state capital in the US, a quaint destination with many quirky attractions to behold. The neoclassical Vermont State House, topped with a gleaming gold dome and flanked by a statue of American Revolutionary War hero Ethan Allen, is a popular landmark worth photographing. Hubbard Park and the banks of the Winooski River are just some of the many arboreal areas suitable for long and leisurely hikes, with the Green Mountains providing a scenic backdrop.
Among the many cultural attractions that will get you interested in Montpelier’s past and present are the Vermont Historical Center, which delves into the state's rich heritage, and the intimate Lost Nation Theater, a venue for top-notch local performances. Just a short drive from Stowe, Montpelier is a perfect day trip or weekend destination.
Grafton
Grafton is the epitome of quirkiness in Vermont, where rolling farmland combines with an artistic and expressive heritage. Tucked away in southern Vermont, this village radiates comfort and ease, especially since Grafton is home to one of the state’s oldest inns, the Grafton Inn, where historic figures such as Ulysses S. Grant, Woodrow Wilson, Ralph Waldo Emerson, and Henry David Thoreau once resided. Visitors to this quaint and quirky town can head over to the Riverledge Farm to appreciate the sustainable agricultural practices that Grafton practices.
Likewise, Plummer’s Sugar House gives newcomers a scrumptious taste of Vermont’s famous maple syrup straight from the source. The Nature Museum, meanwhile, provides insight into the regional ecosystems surrounding Grafton, just as the Jud Hartmann Gallery features compelling bronze sculptures that pay tribute to Native American woodland tribes.
September brings the beloved Fairy House Festival, where whimsical creations line the forest trails, enchanting children and adults alike. Finally, outdoor spots like the John Dorand State Forest and the Grafton Town Forest will keep you engaged and excited about your remarkable journey through Grafton.
Manchester
With the Taconic and Green Mountains surrounding this quirky town, Manchester is a vibrant mountain destination where one can relish in the high-altitude beauty of Vermont. Here, travelers can gain access to the Appalachian Trail and other nearby hiking, biking, and fly-fishing spots in the Battenkill River Valley. A highlight of any visit is Hildene, the stately home of Robert Todd Lincoln, son of Abraham Lincoln, for which you can participate in guided tours of Hildene’s Georgian Revival mansion, gardens, and working farm.
Art and culture thrive at the Southern Vermont Arts Center, a casual and quirky place hosting exhibitions, live music, and summer film screenings on its lush grounds. At the end of the day, you can rest and refresh for a new adventure day in luxurious spots like the Equinox Resort, the Kimpton Taconic Hotel, or The Inn at Manchester.
Weston
As one of Vermont’s most picturesque and panoramic villages, Weston is a thriving community in the Green Mountains. Around 50 minutes from the city of Bennington, Weston was founded in 1799 by settlers from the city of Weston in Massachusetts. The town is home to Vermont’s oldest professional theatre, the Weston Playhouse Theatre Company, which has continued to entertain visitors and townsfolk since its opening in 1935. Likewise, Weston contains the Old Mill Museum, which preserves one of the oldest mills in the area.
Travelers who are more invested in the untamed wilderness of Vermont can venture into the Green Mountain and Finger Lakes National Forests as well as the Okemo State Forest. At last, individuals who are eager to stay a long while in this quirky and calming town can seek out Weston’s fine establishments, such as the nearby Okemo Mountain Resort.
Dorset
Perched along the Mettawee River and just seven miles from Manchester, Dorset is an eccentric and eclectic small town with many artistic and creative appeals. Known for its peaceful pace and mountain setting, Dorset is also the birthplace of Alcoholics Anonymous co-founder Bill Wilson, whose boyhood home, the Wilson House, now serves as a historic lodging and a place of reflection on the 12-step program. Art and culture flourish at the Marble House Project, an artist’s residency housed in the historic Manley-Lefevre House, making Dorset an idyllic location for exploring one’s bizarrely beautiful side. Dorset Quarry, the first marble quarry in the US, now functions as a unique swimming and sightseeing spot for everyone to photograph.
For those seeking more outdoor fun, Cutler Memorial Forest and Emerald Lake State Park are excellent and rewarding regions teeming with trails. Whether you are in town for an art residency, history, or a quiet weekend in nature, Dorset offers warm hospitality at inns like The Dorset Inn or the Aerie Inn for a longer, more relaxing vacation in this quirky Vermont town.
Shelburne
Shelburne, just a few miles south of the city of Burlington, thrives as an accommodating yet quirky homestead on the eastern strand of Lake Champlain. Among the many unique and immersive landmarks to enjoy in Shelburne are the Shelburne Farms, a non-profit organization focusing on the farm-to-table products and techniques that Shelburne farmers are famous for perfecting. Photogenic locations such as Scenic Beach Bench and Coach Barn near Lake Champlain attract hundreds of visitors to their idyllic settings.
For a grand sojourn through the streams of history, you can enter the Ticonderoga Steamboat, a well-preserved vessel that, although no longer capable of braving the water, doubles as an interactive museum depicting the steamboat industry in Shelburn and Vermont. Even more quirky wonders await at the Vermont Teddy Bear Factory, a birthing place for one of the most adorable stuffed animals on Earth.
While Vermont may lack towering skyscrapers, its strength lies in the quiet majesty of the quirkiest Vermont towns you did not know existed in the Green Mountains. These places, each a unique and photogenic marvel, showcase more than just scenic backdrops: they are all opportunities worth experiencing, whether they be historic landmarks, cultural hubs, or nature-sculpted masterpieces. From Stowe's alpine adventures to Dorset's marble legacies and Grafton’s pastoral calm, every town has quirks and attractions that make the journey worthwhile. This year or the next, you should definitely pack your camera and sate your curiosity by visiting some of the quirkiest Vermont towns you did not know existed.
