7 Most Eccentric Towns in Vermont

Ever thought a small town could catch you off guard? Tucked between New York and New Hampshire, Vermont is best known for its covered bridges, green mountains, and quaint villages. Founded in 1791 as the 14th state, Vermont played a key role in early American history, from its independent Republic days to its abolitionist movement. But beneath the postcard-perfect scenery, there are a few towns that embrace the strange, making them unforgettable with their weirdness and off-the-wall traditions. From a museum filled with everyday items to a festival that brings Main Street to a standstill with cows, these towns have more than the typical charm. If you enjoy history with a twist, hit the road and discover these seven strange Vermont towns for an unforgettable adventure.

Glover

Glover is home to one of the country’s strangest museums: The Museum of Everyday Life. Instead of fine art or valuable artifacts, this museum highlights everyday objects like toothbrushes, pencils, and even dust. The self-guided museum invites visitors to contemplate thought-provoking exhibits on the mundane, making it one of Vermont’s strangest attractions. Bread & Puppet Theater, a local oddity, is one of the country’s oldest experimental theater companies. Renowned for its giant papier-mâché puppets and politically challenging performances, the company has been based in Glover since the 1970s.

Despite all its eccentricity, Glover is also naturally gorgeous. Shadow Lake offers a peaceful spot for swimming and kayaking, and the nearby Craftsbury Outdoor Center is a haven for cross-country skiing and cycling. But it’s the town’s enthusiasm for the strange that sets it apart.

St. Johnsbury

It is a town where the strange exists alongside the historic. Dog Mountain, a sprawling sanctuary dedicated entirely to dogs, is unlike anything else in Vermont. Its Dog Chapel, built as a memorial to beloved pets, is covered in poignant messages from visitors. With open fields for off-leash play and trails winding through the hillside, it’s heaven for both dogs and their owners.

Science and wonders converge at the Fairbanks Museum & Planetarium, with exhibits ranging from two-headed calves in taxidermy to an interactive space experience. The town has a sweeter side as well—Maple Grove Farms, the country’s oldest maple candy factory, has been churning out syrupy treats for over a century, giving visitors a taste of Vermont’s signature flavor.

Barre

Barre’s quirkiness is carved in stone—literally. Dubbed the “Granite Capital of the World,” the town is famous for its massive granite quarries and over-the-top, sometimes bizarre gravestones at Hope Cemetery. Monuments here include stone race cars, soccer balls, and even life-sized likenesses of the deceased, earning it recognition as one of the country’s strangest cemeteries. Rock of Ages Quarry lets visitors see where these massive stoneworks are crafted, offering guided tours and even a chance to bowl on a granite lane.

The city also embraces its artistic side. Studio Place Arts showcases local artists, and Millstone Hill has hiking trails with historic quarries now filled with crystal-clear water.

Woodstock

Woodstock is Vermont’s most striking town, but don’t let its postcard façade fool you—there are some quirky surprises beneath the surface. Billings Farm & Museum is not your typical historic dairy farm—it’s also home to an eccentric collection of antique butter churns and cow-themed exhibits. The Middle Covered Bridge, one of Vermont’s most photographed landmarks, is smack in the center of town, offering the quintessential backdrop.

The offbeat aspect of Woodstock is its passion for vintage tractors. The town’s annual Antique Tractor Day sees old farm equipment parading through the streets to the delight of locals and visitors. Those who love nature can explore the Marsh-Billings-Rockefeller National Historical Park, where scenic trails offer a glimpse into the town’s conservation history.

Montpelier

The smallest U.S. state capital, Montpelier is quaint and eccentric with its off-the-beaten-path attractions. What makes it truly quirky is that it’s the only state capital in America without a McDonald’s. Instead of chain fast food, the town embraces small businesses, with places like The Skinny Pancake serving farm-fresh crepes.

The Vermont State House, with its gold dome, contrasts with the town’s more eccentric attractions, like Lost Nation Theater, known for its experimental performances. Independent bookstore Bear Pond Books has been a local staple for years and is renowned for its carefully curated collection of rare finds, local authors, and an entire section dedicated to the history of Vermont. Since 1947, the Montpelier Live Poets Society has hosted spoken word performances, where locals share everything from comedic rants to heartfelt prose, keeping the town’s artistic energy alive and well.

Brattleboro

Brattleboro is one of the most offbeat towns in the state of VT, a haven for artists, musicians, and free spirits. Each summer, the town hosts the Strolling of the Heifers, a tongue-in-cheek parade where cows take over Main Street in a playful twist on Spain’s Running of the Bulls. The Brattleboro Museum & Art Center features changing contemporary art exhibitions, often interactive and experimental. The Gallery Walk, presented on the first Friday of each month, transforms downtown into a vibrant arts celebration, complete with jugglers, live music, and even mock archaeologists good-naturedly “excavating” for UFO remnants. This rain-or-shine affair keeps the town’s creative energy going year-round.

For a different kind of experience, The Estey Organ Museum highlights Brattleboro’s unexpected past as a premier organ manufacturing hub, featuring beautifully restored instruments that once shaped the town’s industrial history.

Shelburne

Few towns embrace eccentricity as wholeheartedly as Shelburne, where history, art, and whimsy converge in unexpected ways. The Shelburne Museum, a vast collection of oddities spread across 39 historic buildings, features everything from a lighthouse and a jail to a full-sized steamship docked in a meadow. The collections range from circus artifacts to offbeat folk art, making it one of the most peculiar museums in New England.

Adding to its quirkiness, Shelburne Farms is a sprawling working estate where visitors can tour a fairy-tale-like mansion, interact with farm animals, and watch cheesemakers craft award-winning cheddar. For an even stranger experience, the Vermont Teddy Bear Factory offers a behind-the-scenes look at the production of custom teddy bears, complete with a “Teddy Bear ER” for stuffed animal emergencies.

Embracing Vermont's Unique Towns

Vermont’s small towns prove that uniqueness thrives in the most unexpected places. From Glover’s Museum of Everyday Life to Shelburne’s steamship-docked-in-a-field museum, each town embraces quirks that set it apart. Some, like Brattleboro, celebrate the bizarre with cow parades and vibrant arts festivals, while others, like Barre, carve personality into granite with larger-than-life cemetery monuments. In Montpelier, even fast food is an afterthought, and Chester’s streets are filled with scarecrows in a seasonal explosion of creativity. From puppet shows to quirky art to towns that reinterpret history, Vermont is a journey through the bizarre, the beautiful, and the wonderfully unexpected.