Main street of Montpelier in Vermont in the fall

6 of the Quirkiest Towns in Vermont

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. 


Summer Farmers Market in Montpelier, Vermont.
Summer Farmers Market in Montpelier, Vermont. Editorial credit: Phill Truckle /

Montpelier my be Vermont's capital, but with only 8,000 inhabitants, it is the smallest capital city of all US states. (The second-smallest — Pierre, South Dakota — is sizably larger, with 14,000.) Settled in 1787, the historic town beckons the visitor with a large set of landmarks, from the Vermont History Museum to the nearly 200-acre Hubbard Park. The State House is also open for public visits. For one of the northeast's most celebrated watersides, Lake Champlain sits less than an hour's drive west.

The town takes its name from Montpellier, a city in the south of France. Vermont's counterpart was named during a high point of admiration for the French, given their support to colonial forces in the US War of Independence. The town's other unusual features include its history of flooding, with historic damage done in the years 1927, 1992, and most recently in 2023. 


Lake Elmore State Part with beautiful autumn foliage and water reflections at Elmore, Vermont
Lake Elmore State Part with beautiful autumn foliage and water reflections at Elmore, Vermont

With fewer than 900 residents, Elmore, in Lamoille County in the state's north-central zone, is a quiet, beloved destination for autumn leaf-peepers. And the small town north of Montpelier offers a few quirks of its own, not least the simple fact that numerous local landmarks are named 'Elmore.' Elmore town is separate from East Elmore. Elmore Mountain rises to the town's west. Elmore State Park sits north of Elmore proper, while Elmore Lake offers waterside bliss, and is routinely named among the prettiest lakes in the state. The lake drains via Elmore Pond Brook into the Lamoille River

Like Montpelier, Elmore sits east of Lake Champlain. Visitors needing a city break, or a few less Elmores, can head to trendy Burlington, an hour's drive west. 


Aerial view of Stowe Vermont and autumn colors.
Aerial view of Stowe Vermont and autumn colors.

Stowe, population 5,300, draws adrenaline junkies and other eccentrics as Vermont's number-one ski and snowboard town. The Stowe Mountain Resort claims it is the "ski capital of the east," meaning the eastern United States. Located near the majestic Mount Mansfield, Stowe provides fun in warmer weather, too. Hiking and mountain biking are popular in nearby Cady Hill Forest. 

Stowe was once the home of Jake Burton Carpenter (1954-2019), founder of the Burton Snowboards company and a pioneer in making snowboarding an international sport. If he was called eccentric for starting the company back in 1977, Vermonters and others now see him as a visionary. His legacy continues to inspire younger competitive types, like those who attend Mount Mansfield Winter Academy, a special school for aspiring snow sports champions. 


View of the historic and colorful Manchester Village in Manchester, Vermont with tulips in bloom
View of the historic and colorful Manchester Village in Manchester, Vermont with tulips in bloom

Manchester, with 4,500 inhabitants, sits in southwest Vermont. The town is a favorite among lovers of the arts and architecture. Hildene, the name of the estate of Abraham Lincoln's son Robert, includes an enormous Georgian Revival home and grounds. The town's American Museum of Fly Fishing, with its displays of rods, flies, and paraphernalia, draws all kinds of superstitious anglers. Manchester is the headquarters of Orvis, the fishing and clothing company. The Southern Vermont Arts Center organizes exhibits, and has a sculpture garden and performing arts space. Nature fans should head to Mount Equinox, west of town, otherwise to the Green Mountain National Forest to the south. 

Eccentric fact: Jonathan Goldsmith, famous as the actor who played "The World's Most Interesting Man" in the Dos Equis beer commercials, lives in Manchester. Stay quirky, my friends. 


Historic downtown of Brattleboro, Vermont.
Historic downtown of Brattleboro, Vermont. Image credit jenlo8 via Shutterstock

Brattleboro, population 12,100, sits on the Connecticut River and offers ample draws and oddities. Lying just west of New Hampshire (the Connecticut River divides the states) just north of the Massachusetts border, the town serves as a convenient middle point for touring the broader New England area. Outdoors fans will enjoy Fort Dummer State Park, where hikers, bikers, and campers are welcome.

Among history's more famous oddballs, the British writer Rudyard Kipling settled in Brattleboro after marrying a Vermont woman in 1892. Their house is named Naulakha, a nod to the writer's birth and early childhood in India. Kipling felt that Brattleboro's oppressive small-town culture gave its residents a "terrifying intimacy" in each another's lives. Was Kipling the quirkiest, or his Brattleboro neighbors? 


Snowy day at the farm in Woodstock.
Snowy day at the farm in Woodstock. Editorial credit: James Kirkikis /

Woodstock, separate from the town and 1969 cultural moment in upstate New York, has 3,000 residents. This southeastern town attracts architecture buffs, not least for the First Congregational Church, first built in 1807, with a bell cast by American revolutionary Paul Revere; and for the Norman Williams Public Library, finished in 1884. For fresh air, take a walk in Woodstock Town Forest, south of town.  The Marsh Billings Rockefeller National Historical Park offers sweeping views of the region. It is the only part of the US National Park system in Vermont aside from the Appalachian Trail. 

More recently, Woodstock has built up a more modern infrastructure by advancing digital technology. Since 2011, the "Wireless Woodstock" plan has covered the entire town with free internet. Not quirky, 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. 

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