15 Most Charming Small Towns in Vermont

Vermont, a state as quaint as it is rugged, invites you into its fold with open arms. Nestled against Canada’s border, its terrain unfolds in a pageant of rolling mountains and serene lakes, each scene a testament to nature’s artistry and the state’s storied past.

As skiing trails transform with the seasons into hikers’ and bikers’ havens, small towns, with their resilient histories and narrated walls, beckon you to linger a little longer.

You are transported back to the dawn of America as you meander through the sleepy towns scattered like jewels across Vermont’s landscape. Here, every historic structure and local legend weaves an intricate tapestry of the tapestry of the state’s colonial and national heritage.

Each town is a unique vignette, inviting you to explore its beauty and depth of character.

15. Bennington: A Glimpse of Revolutionary History

Discover the towering Bennington Battle Monument, an impressive 93-meter obelisk that stands as the tallest structure in Vermont. It commemorates a pivotal 1777 battle in the American Revolution.

Just a short distance away, you’re invited to explore the Park-McCullough House, an exquisite specimen of Victorian architecture that offers public tours.

As you stroll through downtown Bennington, let yourself be transported back over two centuries, surrounded by historic buildings that silently narrate the tale of this town’s early days.

14. Warren: A Gem in the Green Mountains

Nestled within the Mad River Valley, you’ll find Warren, a quintessential Vermont town embraced by the verdant slopes of the Green Mountains.

Since the 1930s, this area has been a haven for snow sports enthusiasts, thanks to its pioneering ski lift—the first step in transforming Warren into a winter retreat. By the 1950s, even the iconic Kennedy family gravitated here to carve through the snow.

During summer, the town reveals a different charm. Warren Falls invites you with its crystalline waters, offering a serene escape from summer’s warmth, set against a backdrop of mountain grandeur. This town is as much a spectacle in the heat as under a blanket of snow.

13. Middlebury: A Historical Haven

Enveloped by Addison County’s pastoral splendor, your journey through Vermont’s history isn’t complete without a visit to Middlebury. Here, the Henry Sheldon Museum is a testament to state heritage, offering a unique glimpse into Vermont’s past through its exquisite collection of art and antiquities.

The charm of Middlebury extends to its proximity to Lake Dunmore, where nature trails beckon outdoor enthusiasts for cycling and treks. For moments of peaceful reflection, Battell Park’s trails through lush greenery offer a serene escape from the bustle.

• Henry Sheldon Museum: Art and antique exhibits showcasing Vermont’s history
• Vermont Folklife Center: Dedicated to cultural traditions
• Lake Dunmore: Ideal for biking and hiking
• Battell Park: Tranquil nature walks

See Related: Best Places to Visit in Vermont

12. Encounter Waterbury

Waterbury invites you for year-round outdoor adventures amidst the majestic Green Mountains. In winter, embrace the thrill of the slopes with skiing or partake in unique experiences like snowshoeing and dog sledding. The snow-laden paths also set the stage for romantic sleigh rides under the Vermont sky.

With spring’s thaw, the forests beckon hikers and campers. Waterbury is a hub for sampling Vermont’s finest, such as fresh Cold Hollow Cider Mill cider and coffee at the Green Mountain Coffee Shop. Don’t miss the chance to indulge in the celebrated flavors of Ben & Jerry’s Ice Cream right from its birthplace.

11. Exploring Burke

Nestled near a majestic 1,000-meter peak, Burke offers superb skiing opportunities at the Burke Mountain Ski Area when winter cloaks the landscape in white. In summer, those same slopes welcome you to scenic hiking adventures.

The community-supported mountain biking trails in Burke transform into serene cross-country ski paths as the seasons change. For those sun-soaked days, the crystalline waters of Lake Willoughby and Lake Crystal beckon you for refreshing swims.

If roaming is your rhythm, the trails around Mount Hor and Mount Pisgah provide ample grounds for discovering the area’s natural splendor.

10. Exploring Hartford

Nestled at the juncture where the White, Connecticut, and Ottauquechee Rivers meet, Hartford is a quaint compilation of five unique villages, each boasting its individual history since the town’s establishment over 50 years ago.

You’ll find Hartford to be a town where waterways and railways converge, a nod to its industrial past, which, in the 1800s, sawmills rise, and the hum of train tracks signal prosperity.

Board the Amtrak Vermonter—your daily connection to New York—and step off into a town that’s held onto its modest allure. Spend time meandering downtown, popping into mom-and-pop shops, or enriching your knowledge at local haunts like the Main Street Museum.

Later, lose yourself in a performance at the Northern Stage Theater, where Hartford’s artistic pulse comes to life.

9. Weston: A Snapshot of Tradition

Tucked in Windsor County, Weston invites you with its timeless allure – a window to Vermont’s storied past. Amble through the town center where the 1832 Old Parish Church stands, its history mingling with the serenity of the present. Nearby, the Village Green Gallery offers a warming blend of art and coffee.

Seek the comforts of the Inn at Weston, established in 1848, and indulge in a morning meal that will ready you for the day.

For a moment of tranquility, visit the Weston Priory. Here, the Benedictine Monks open their chapel for communal reflection, enriching your experience of Weston’s serene community tapestry.

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8. Waitsfield: A Pastoral Gem

Nestled between the Green and Northfield Mountains, Waitsfield embraces you with its verdant valleys, peppered with heritage farmhouses harkening back to an era when agriculture was the town’s heartbeat.

Today, these longstanding homes welcome you as charming bed-and-breakfasts, offering a tranquil retreat amongst nature’s splendor.

As you meander through Waitsfield, your palate is tempted by an array of gastronomic delights. Whether your preference leans towards robust Mexican flavors, the simplicity of vegetarian dishes, or the indulgence of French cuisine, your taste buds will find satisfaction here.

To complement your meal, savor the local craftsmanship with a sip of the town’s own IPA, as distinctive as Waitsfield.

7. Discovering Shelburne by the Lake

Nestled against the expansive Lake Champlain, Shelburne captivates with its sparkling waterfront, which extends across 514 square miles into Quebec.

Your summer visits here are incomplete without indulging in watersports, embracing the art of yachting, or simply lounging by the beach as the sun sets over the horizon.

In the heart of Shelburne, the Shelburne Museum awaits, boasting an eclectic mix of fine impressionist art and American oddities. It’s a place where you can step aboard a rare gem—a side-paddle-wheel steamer—and immerse yourself in the echoes of its nautical past.

6. Discover Stowe

Nestled among Vermont’s Green Mountains, Stowe is synonymous with snow-capped slopes and skiers silhouetted against Mount Mansfield, Vermont’s apex. Stowe’s 19th-century charm persists downtown, where historic storefronts invite you to meander.

• Stowe Community Church: An enduring symbol with a steeple piercing the sky since 1863
• General Store: A stalwart of commerce since 1895
• Stowe Theater Guild: Marvel at local performing arts

In between sightseeing, the Stowe Public House welcomes you with the warmth of craft beers—a toast to your mountain town adventure.

5. Discovering Grafton

Nestled within Vermont’s picturesque landscape, Grafton enchants with its quaintness and a sense of time standing still.

Rewind to 1791, where an auction involving just $5 and some rum granted the right to rechristen Thomlinson to Grafton, echoing the bidder’s sentiment for his Massachusetts hometown.

Your eyes won’t find the modern clutter of electrical and phone lines here; thanks to the Windham Foundation’s efforts in the ’60s, these amenities gracefully tuck below ground. This act is a loving nod to Grafton’s past, ensuring its streetscape remains untarnished.

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4. Discovering Dorset

Dorset holds a significant place in history as a key player in establishing what was once the Vermont Republic in the latter part of the 17th century.

Your journey here leads you to the oldest marble quarry in the US, which has contributed its fine stone to the iconic New York Public Library.

Although quarrying operations are no longer active, the site now serves as a favored summer gathering place for swimming and cliff jumping.

Encircling Dorset, the inviting trails call for exploration, setting the stage for outdoor adventures. You can traverse the landscape near Dorset Mountain, a destination that promises more than mere views but a connection to the great outdoors.

This small town encapsulates an element of the state’s enduring charm, where history and nature combine to create an enriching experience for the traveler in search of both.

3. Discovering Woodstock

As you wander the streets of Woodstock, you can’t help but be enveloped by its storied past. The Woodstock Village Historic District showcases architectural treasures from the 18th and 19th centuries, including the well-preserved Norman Williams Public Library.

Venture to the outskirts, and you’ll uncover the enchanting realm of Marsh-Billings-Rockefeller National Historical Park.

Meander through its verdant landscapes, and eventually, you’ll stumble upon the Billings Farm and Museum—an emblem of forward-thinking agricultural practices initiated in the 1890s and once under the stewardship of Laurance Rockefeller.

A testament to the town’s profound connection to history and nature, your journey through Woodstock is an immersion into a living, breathing storybook.

2. Chester: A Snapshot of New England Charm

Amidst the quiet hum of New England, you’ll discover Chester, a cozy nook where history papers the walls of its downtown. As you wander Main Street, historic storefronts and houses invite you to explore leisurely.

This slice of the past, established in 1761, is home to landmarks like the Old Train Station and the Stone Village—a testament to Chester’s storied foundations.

While the Vermont green cloaks the town, Chester’s festivals brim with vibrancy, from the Big Buzz Chainsaw Carving Festival to the Chester Fall Festival and spirited winter celebrations.

Each event stitches a thread of enthusiasm through the community tapestry, ensuring your visit is painted with local color, regardless of the season.

1. Manchester: A Snapshot of New England’s Charms

Uncover Manchester’s heart-stealing essence, from its postcard-worthy steeples to the storied Bennington County Courthouse and the historic elegance of Hildene, the ancestral summer retreat of the Lincoln lineage. Beyond its architectural delights, Manchester beckons outdoor enthusiasts throughout the seasons.

Carve the snowy slopes of Bromley Mountain in winter, while in summer months, dare you to soar across some of the state’s lengthiest zip lines. Y

ear-round, the expansive Green Mountain National Forest offers nearly 400,000 acres of raw, natural playgrounds to those preferring their adventures on foot, bike, or stroll.