Vermont is, for many visitors, the postcard-perfect New England state. A part of the United States since 1791, the first to join the Union after the Thirteen Original Colonies, Vermont has many unique, and sometimes quirky, features. The place has attracted artists and other creative geniuses, some of them decidedly eccentric, from its earliest days. The natural parts of Vermont, like the famous Lake Champlain, offer unusual points of interest for visitors and locals alike. With a state as rich in traveling attractions, it should be little wonder that some of them come with a quirk or two.

Montpelier

Montpelier, while being Vermont’s charming capital, is the tiniest among all US state capitals with just around 8,000 residents. For comparison, the second-smallest, Pierre in South Dakota, has a population of about 14,000. Established in 1787, this historic town warmly welcomes visitors with a variety of landmarks, including the Vermont History Museum and the sprawling 200-acre Hubbard Park. The State House is also open to the public for tours. Just a short drive west, less than an hour away, lies Lake Champlain, one of the Northeast’s most beloved watersides.

The town’s name pays homage to Montpellier, a beautiful city in southern France. This naming reflected the high regard for France at the time, especially for their support during the US War of Independence. Interestingly, Montpelier has experienced its share of flooding, with significant damage occurring in the years 1927, 1992, and most recently in 2023.

Elmore

Elmore, a charming small town in Lamoille County with fewer than 900 residents, is a favorite spot for autumn leaf-peepers. Located north of Montpelier, this peaceful town has its own unique charm, including several local landmarks sharing the name ‘Elmore,’ which adds to its character. It’s important to note that Elmore town is separate from East Elmore. To the west, Elmore Mountain overlooks the area, while Elmore State Park lies just north of the town itself. Enjoying waterside beauty, Elmore Lake is often listed among Vermont’s most picturesque lakes, with its waters flowing into the Lamoille River through Elmore Pond Brook. Like Montpelier, Elmore is situated east of Lake Champlain. For those seeking a more bustling scene or a change of pace, the vibrant city of Burlington, just an hour’s drive west, makes for a perfect day trip or weekend getaway.

Stowe

Stowe, with a lively population of 5,300, is Vermont’s top spot for adrenaline seekers and the eccentrics among us, earning its reputation as the state’s premier ski and snowboard destination. The Stowe Mountain Resort proudly calls itself the “ski capital of the east”—that’s the eastern United States. Nestled near the breathtaking Mount Mansfield, Stowe offers more than just winter fun; warmer months bring plenty of activities like hiking and mountain biking in the beautiful Cady Hill Forest.

The town also has a rich history, being the home of Jake Burton Carpenter (1954-2019), the visionary behind Burton Snowboards and a trailblazer in making snowboarding an international sport. While some might have called him eccentric when he launched his company in 1977, today he’s celebrated as a true pioneer whose legacy keeps inspiring young snow sports enthusiasts, like those at Mount Mansfield Winter Academy, a special school dedicated to nurturing the next generation of champions.

Manchester

Manchester, a town with 4,500 residents located in southwest Vermont, is popular among art and architecture enthusiasts. It features Hildene, the estate of Abraham Lincoln’s son Robert, which boasts an impressive Georgian Revival house and grounds. The town’s American Museum of Fly Fishing showcases numerous rods, flies, and related gear, attracting many superstitious anglers. Manchester is also home to Orvis, a renowned fishing and clothing company. The Southern Vermont Arts Center hosts exhibitions, and includes a sculpture garden and performance space. Nature lovers should visit Mount Equinox, west of town, or explore the Green Mountain National Forest to the south.

Eccentric fact: Jonathan Goldsmith, known for portraying “The World’s Most Interesting Man” in Dos Equis commercials, resides in Manchester. Stay quirky, my friends.

Brattleboro

Brattleboro, with a population of 12,100, sits along the Connecticut River and features a variety of attractions and oddities. Located just west of New Hampshire—in which the Connecticut River forms the border—and just north of Massachusetts, the town is an ideal midpoint for exploring the wider New England region. Outdoor enthusiasts will appreciate Fort Dummer State Park, welcoming hikers, bikers, and campers alike. Among the more renowned eccentric figures in history, British writer Rudyard Kipling moved to Brattleboro after marrying a Vermont woman in 1892. Their home, Naulakha, references his birth and childhood in India. Kipling believed that Brattleboro’s conservative small-town culture created an

Woodstock

Woodstock, a town with 3,000 residents located in upstate New York, is separate from the famous 1969 cultural event. This southeastern town attracts architecture enthusiasts, particularly for the First Congregational Church, built in 1807 and featuring a bell cast by American revolutionary Paul Revere, and the Norman Williams Public Library, completed in 1884. For outdoor activities, visitors can walk in Woodstock Town Forest, located south of the town, or enjoy panoramic views from the Marsh Billings Rockefeller National Historical Park, the only part of the US National Park system in Vermont besides the Appalachian Trail. Recently, Woodstock has modernized its infrastructure with digital technology, launching the “Wireless Woodstock” initiative in 2011, which provides free Wi-Fi across the entire town. It’s not quirky; it’s just cool.

Vermont’s Quirky Small Towns May Also Be Its Best

These small Vermont towns show the state’s sometimes quirky, but never boring character. Architecture fans will find unusual, beautiful examples state-wide. Montpelier is an oddly pint-sized capital with heavyweight history. Brattleboro has long attracted strange, sometimes brilliant types, whether foreign or domestic. Manchester is interesting enough for the World’s Most Interesting Man. And with abundant natural parks, the Green Mountains, and the majesty of Lake Elmore and Lake Champlain, the quirks of Vermont’s best features should attract even the most straight-laced visitors.