The 15 Best Towns in Vermont That We Might Just Move to

editor@purewow.com (PureWow)
·9 min read

Vermont is known for its verdant mountains, fall foliage and New England charm. Looking to peep colorful leaves, conquer peaks, shack up at a cozy B&B, sample fresh-tapped maple syrup and shop for antiques? The Green Mountain State never ceases to amaze.

Scroll on for the best towns Vermont to add to your must-visit list.

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1. STOWE, VT

Ready to hit the slopes? Nestled in the northern corner of Vermont, Stowe is a ski-lovers paradise. Even when there isn’t a fresh cost of powder on the ground, Stowe lures outdoor adventurers with the promise of forested trails and 1,000-foot cliffs at Smugglers’ Notch State Park. While Moss Glen Falls offers scenic cascades and crystal-clear pools to take a dip. For more open-air excitement, we suggest a trip to West Branch Gallery & Sculpture Park.

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2. WOODSTOCK, VT

Woodstock perfectly encapsulated everything you’d want in a Vermont getaway. It’s a cute town packed with colonial architecture, farm-to-table restaurants and craft brewers (swing by Long Trail Brewing Company for a VT IPA). On the rustic appeal front, we’re big fans of the Billings Farm & Museum, which were once owned by Laurance and Mary French Rockefeller. Woodstock also has a thriving arts community. So you can scoop up landscape paintings, plaid textiles or hand-carved wood bowls to bring a piece of the Green Mountain State back home.

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3. BENNINGTON, VT

Some know Bennington as Vermont’s first town (it was chartered way back in 1749), others recognize it from the legendary stories of Ethan Allen and the Green Mountain Boys. Visitors can book a walking tours of the historic downtown and admire one of the best enduring examples of Victorian architecture at the Park-McCullough Historic Governor's Mansion. Another claim to fame? The Bennington Battle Monument is the tallest man-made structure in the entire state.

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4. SHELBURNE, VT

Shelburne is the unsung hero of Vermont destinations. That’s because this Burlington suburb that’s perched along the shores of Lake Champlain lives in the shadow of its big-city neighbor. But, if you ask us, there’s plenty to fill a weekend. Stop by Shelburne Farms to learn about sustainable agriculture practices, do a guided birdwatching walk and savor delicious field-to-fork fare. Don’t forget to visit the Flying Pig Bookstore and the impressive art collection at the Shelburne Museum.

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5. MANCHESTER, VT

We dare you to name a place more charming than Manchester. The enchanting downtown area is filled with cute boutiques, quaint inns, cafes and top-rated restaurants such as Ye Olde Tavern. Another major selling point? Access to stunning scenery. Insert Equinox Preservation Trust and Lye Brook Falls. History buffs won’t want to miss Hildene, the Lincoln family summer home. Be sure to stock up on fresh-picked veggies and homemade pesto at Earth Sky Time Community Farm before departing.

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6. GRAFTON, VT

Tucked away in the mountains of southern Vermont, Grafton oozes alpine charm. It has just 619 residents (for reference, that’s a population density of 18 people per square mile). So, yea, we’re talking about a very small town. Size aside, you’ll swoon over the covered bridges, lovingly restored historic buildings—including the iconic white-steepled church and brick meetinghouse—grassy meadows and farm stands selling raw milk. The Nature Museum is certainly worthy of a visit, too.

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7. MIDDLEBURY, VT

Sandwiched between the Green Mountain foothills and the verdant low-lying Champlain Valley, Middlebury is a place of unparalleled beauty. This undeniably picturesque town does more than attract travelers with its visual attributes and access to a wealth of outdoor activities (hiking, biking, fishing, canoeing and skiing to name a few). It’s a burgeoning culinary hotspot with restaurants serving locally grown produce, pasture-raised meats and fresh cheese. Middlebury also houses the Henry Sheldon Museum of Vermont History.

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8. BRATTLEBORO, VT

Dubbed “the artistic and energetic hub of southern Vermont,” Brattleboro exudes a creative sort of vibe (the word “crunchy” comes to mind) that’s often imitated but never replicated. This hippie-leaning town located just over the border from Massachusetts intrigues and delights at every turn. You’ll find breweries, distilleries, museums, galleries, shops and restaurants. There’s even a stunning Art Deco theater that screens indie films. Would you expect anything less from Brattleboro? Nope, us either.

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9. QUECHEE, VT

A small town with a big list of scenic diversions, Quechee (pronounced kwee-chee) earns our vote for a picture-perfect New England getaway. In the fall, leaf peepers flock to see the shades of red, orange and yellow. The annual Quechee Hot Air Balloon, Craft & Music Festival goes down in June. Housed in a restored 19th-century mill that overlooks a gushing waterfall, Simon Pearce's turbine-powered glassblowing studio, flagship store and farm-to-table restaurant is a splendid year-round attraction.

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10. MONTPELIER, VT

With a population of 7,900, Montpelier ranks as America’s smallest state capital. Maple syrup is big business in this twee town. Because no trip to Vermont would be complete without sampling the sweet stuff straight from the source, we highly recommend heading over to Bragg Farm Sugar House. Hungry for more local flavors? Nibble farm-fresh chèvre at Capital City Farmers Market. Definitely add a historic walking tour of downtown Montpelier to your itinerary as well.

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11. CHESTER, VT

The past is very much alive in Chester, an endlessly charming town in the Green Mountains where history and hospitality are basically tied FTW. Houses made of locally quarried slabs dot the Stone Village Historic District. While Chester Village Historic District showcases a fascinating mix of Victorian and Federal-style buildings. You can’t walk a block without a friendly local flashing a warm smile and offering some advice about where to grab a bite or browse the best selection of antiques.

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12. WAITSFIELD, VT

Whether you dig the great outdoors, delicious food or history (how about all of the above?), Waitsfield delivers. This heritage-rich town in the Mad River Valley is a feast for the senses. Navigates paths through timberlands, waterfalls and a beaver pond at Scrag Mountain Town Forest. Step back in time while touring the Madsonian Museum of Industrial Design. Pick up some local treats at one of the many farm stands. Then hop in the car and go for a drive along scenic Route 100.

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13. WESTON, VT

Weston serves up heritage and scenic beauty on a silver platter. Haven’t heard of this tight-knit community until now? Let us fill you in on a few of the many reasons to visit. The idyllic downtown houses historic homes, general stores, eateries (Mildred's Grill is a local favorite), antique shops, the famous Vermont Country Store and the Weston Playhouse Theatre Company. Prefer to spend time surrounded by nature? Explore the sprawling 7,466-acre Okemo State Forest.

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14. DORSET, VT

For a major dose of quintessential New England magnetism, head to Dorset. It really doesn’t matter the time of year because there’s always something lovely to do. Winter calls for skiing at nearby Bromley Mountain. While Emerald Lake State Park provides ample opportunities for hiking in the spring, summer and fall. Such a unique combination of small-town ambiance and a seemingly endless array of activities makes it a terrific spot to visit (though, we wouldn’t mind living in Dorset either).

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15. GREENSBORO, VT

Set in the rugged northern corner of the state, Greensboro has a wide range of rural pursuits that appeal to travelers of all ages. Wander through Barr Hill Natural Area. On a clear day, you'll see spectacular views of the nearby mountains. When the weather warms up, Caspian Lake is a popular spot for water skiing, sailing and kayaking. Don’t leave without visiting Willey's Store to fill your tank and get some locally made products for the road.

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