9 Underrated Vermont Destinations Finally Getting Attention

Vermont, a land of maple syrup dreams and lush green mountains, holds secrets that only the most curious travelers uncover. While many flock to Stowe or Burlington, there are corners of this charming state waiting to delight your senses and surprise your Instagram followers. Grab your camera, your sense of adventure, and maybe a pair of snow boots; because Vermont’s hidden wonders are calling.

1. Grafton

Grafton
© Journeys and Jaunts

Imagine a village where time seems to pause, and you’ve got Grafton. This picturesque gem offers a blend of history and stunning landscapes that’ll have your camera begging for more. Walking down the tree-lined streets feels like stepping into a painting: every building, a brushstroke of pure Americana.

Grafton is an embodiment of New England charm, complete with white clapboard houses and a general store that seems straight out of a storybook. The cheese here is legendary, and you can’t leave without sampling a slice or two at the Grafton Village Cheese Company.

As autumn paints the trees with vibrant hues, Grafton becomes a cozy retreat where nature and nostalgia dance in harmony. It’s a place where every corner whispers history, and every breeze carries a hint of adventure.

2. Island Pond

Island Pond
© Pixels.com Licensing

In the Northeast Kingdom lies Island Pond, a serene haven that’s been waiting patiently for its moment in the spotlight. Known for its tranquil lake, this spot offers a slice of solitude perfect for those needing a break from the hustle and bustle.

Island Pond, often dubbed the “Snowmobile Capital of Vermont,” transforms into a winter wonderland, making it a thrill-seeker’s paradise. But don’t let that overshadow its summer allure; kayaking across the glassy water is nothing short of magical.

The village is small, but its heart is big. Friendly locals and quaint eateries make every visit feel like coming home to a place you’ve never been. It’s an enchanting escape where your only concern is what adventure you’ll embark on next.

3. Quechee Gorge

Quechee Gorge
© vermont_igers

They call it Vermont’s Little Grand Canyon, and it’s not hard to see why. Quechee Gorge is a dramatic sight that leaves even the most seasoned adventurers breathless. Stretching 165 feet deep, it’s a masterpiece carved by glacial activity and the flowing Ottauquechee River.

Stand on the bridge and feel the thrill as you peer into the depths below. The hike around the gorge offers panoramic views that shift with the seasons, each more spectacular than the last. In fall, the burst of color is a visual symphony that’s nothing short of a masterpiece.

Nearby, the village of Quechee offers delightful distractions like glassblowing at Simon Pearce or wandering through the Quechee Antique Mall. A visit here promises a blend of nature’s grandeur and human creativity.

4. Chester

Chester
© Old House Dreams

Welcome to Chester, a small town with a big personality. Known for its Stone Village, this enchanting locale boasts historic architecture that whispers stories of bygone eras. Each stone house is a testament to craftsmanship and resilience, standing proudly amid the modern world.

Strolling through Chester feels like wandering through a living museum. The charming shops and cafes invite you to linger over a cup of coffee and a good book, while the local artisans showcase skills passed down through generations.

The town’s vibrant community offers year-round events, from craft fairs to theatrical performances. And in winter, a dusting of snow transforms Chester into a scene straight from a holiday card. Here, history and hospitality go hand in hand, making every visit unforgettable.

5. Brandon

Brandon
© Brandon.org

Brandon is where creativity and community converge in perfect harmony. This lively town bursts with art galleries, studios, and a spirit that’s as colorful as its streets. Once a bustling mill town, Brandon now thrives as a cultural hub where every corner has a story to tell.

The Brandon Artists Guild is a must-visit, showcasing local talent that ranges from the whimsical to the profound. And if your stomach rumbles, fear not; the local eateries serve up flavors as diverse as the town’s artistic creations.

Brandon isn’t just a place; it’s an experience. The annual “Brandon Independence Day Celebration” is legendary, a festival that brings folks together in a raucous celebration of small-town pride. Here, you’re not just a visitor; you’re part of the family.

6. Montpelier

Montpelier
Image Credit: Ted Dawson, licensed under CC BY-SA 4.0. Via Wikimedia Commons.

Montpelier might be the nation’s smallest capital, but it’s packed with allure. This charming city is a delightful blend of politics, history, and a dash of quirkiness. Nestled among mountains, it boasts a downtown area brimming with eclectic shops and delightful eateries.

The Vermont State House, with its gleaming golden dome, stands proudly as a beacon of civic pride and architectural beauty. It’s a must-see for anyone who enjoys a side of history with their wanderlust.

Beyond politics, Montpelier’s vibrant cultural scene includes everything from local theater to farmers’ markets. Each visit feels like a warm embrace, where every stranger offers a smile, and every moment holds potential for discovery. It’s no wonder this little city is finally getting its due.

7. Weston

Weston
© The Vermont Country Store

Weston is a theatrical delight wrapped in pastoral beauty. Famous for the Weston Playhouse, this town is a haven for art lovers and dreamers alike. It’s where Broadway meets the countryside, offering performances that rival the big city but with a unique Vermont twist.

The town green, with its picturesque bandstand and charming shops, invites you to take a leisurely stroll and soak in the serene ambiance. Every summer, the playhouse opens its doors to visitors eager to experience world-class theater in an intimate setting.

Weston’s allure doesn’t end with the arts. The Vermont Country Store is a nostalgic journey through history, offering everything from penny candy to vintage toys. It’s a place where every visit is a new adventure, and every adventure is a story worth telling.

8. Woodstock

Woodstock
© Geovea

Woodstock, a tapestry of quintessential New England charm, is a place where every season paints a different masterpiece. Known for its iconic covered bridges and rolling hills, this town is as picturesque as a postcard.

The Marsh-Billings-Rockefeller National Historical Park offers an immersive journey through conservation history, while the town itself overflows with artisanal boutiques and cozy cafes. It’s a haven for those who appreciate the finer things in life, wrapped in a warm blanket of small-town hospitality.

In the fall, Woodstock becomes a kaleidoscope of color, drawing leaf-peepers from far and wide. Yet, it maintains a tranquility that makes every visit feel like a gentle escape into nature’s embrace. It’s a place where beauty and peace coexist in perfect harmony.

9. Middlebury

Middlebury
© Caleb Kenna Photography

Middlebury, a college town with a twist, offers more than just academia. It’s a place where history, culture, and natural beauty converge, creating a vibrant community that welcomes all.

The town’s centerpiece, Middlebury College, boasts stunning architecture and a campus that invites exploration. Off-campus, the historic downtown area is alive with bookstores, cafes, and a delightful local bakery that’ll have you coming back for seconds.

For the nature enthusiast, the nearby Green Mountains offer trails that range from leisurely strolls to challenging hikes. Middlebury is a blend of intellectual curiosity and outdoor adventure, providing a backdrop where every visit feels refreshingly new. It’s a community where possibilities are endless, and every street is a new story waiting to be written.

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