8 Adorable Towns for Your Next Vermont Getaway

With a thriving art scene, rich historical background, and plenty of locavore-pleasing restaurants, rustic Woodstock has no problem attracting visitors. Check in at the Woodstock Inn & Resort, a horseshoe-shaped colonial lodge built in 1969 by none other than Laurance Rockefeller. The hotel is heavy-handed when it comes to New England charm, featuring huge stone fireplaces, Audubon prints (from Rockefeller's personal collection), and a vintage game room decked out in plaid Vermont Flannel textiles. Venture 10 minutes from town and you’ll happen upon Long Trail Brewing Co., just one of VT's numerous craft brewers. Inspired by Munich’s Hofbräu House, the riverside pub and restaurant has plenty to offer in the way of handcrafted beer and industrial design. If you’re in need of an early morning meal before you get to drinking, drop by Mon Vert Cafe in Woodstock Village. The cozy coffee shop takes pride in its organic, locally-sourced menu serving up Vermont apple cider mimosas, butterbeer lattes, classic egg sandwiches, and a whole lot more.

Tucked away in the northernmost reaches of Vermont—just an hour or so from the border of Quebec, Canada—Stowe is known for its ski slopes. But whether your visit sees snow on the ground or not, it’s worth spending an afternoon at Smugglers’ Notch State Park, a narrow pass of 1,000-foot cliffs that traverses the Green Mountains. Take in more of the scenic town with a trip to the West Branch Gallery & Sculpture Park. The indoor/outdoor art space displays all types of media—photography, paintings, sculptures—from mid-career artists. When it comes time to rest, consider bedding down at one of Stowe’s most modern stays. Contrary to popular belief, Vermont isn’t all quaint B&Bs—just look to Field Guide for a taste of the state’s design-led boutiques. Thirty guest rooms range from apartment-like suites to standalone cottages, mixing woodsy decor (think papier-mâché taxidermy and bird print wallpaper) with plush amenities like kimono robes and Lather bath products.

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If you make the trip to Vermont—the maple syrup capital of the United States—and you don’t leave with a stash of the homemade treat, you’re doing something seriously wrong. To remedy this, start your Montpelier stay with a stop by Bragg Farm Sugar House, a family-run business that’s taught eight generations the secret to crafting perfect maple kettle corn, cookies, and candies. From there, it’s over to stylish creperie, The Skinny Pancake, to further indulge with sweet and savory options like the Pure and Simple, with Cabot butter, granulated sugar, local syrup, and the Sass-Squash, with butternut squash, VT chèvre and apples, and organic spinach. Before you’re forced to leave the foothills of the Green Mountains, fit in one last food-fueled event. Swing by the Capital City Farmer’s Market so you can pick up farm-fresh produce that supports local growers.

One look at Grafton’s historic covered bridges, romantic country inns, family-run farmsteads, and sheep-dotted pastures, and you’ll realize that the village is a representation of small town New England at its finest. Nestled in Vermont’s Green Mountains, the charming town is home to less than 600 year-round residents who regularly convene for Town Meetings (see Gilmore Girls’ Stars Hollow, for reference). Tuck your things away at Main Street’s circa-1801 Grafton Inn—right next door to the village’s iconic white steepled church—and make a beeline for Grafton Village Cheese Co. We'd argue that there's no better way to spend an afternoon than nibbling on naturally-aged, handmade variations (there’s more than 80) like truffle cheddar, 18-month emmentaler, and sheep gouda while you watch the company’s cheesemakers in action.

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With Green Mountain foothills to the east, and the rolling pastures of Champlain Valley to the West, Middlebury makes itself at home in one of Vermont’s most scenic regions. The less-than-10,000-person town is perhaps best known for its eponymous college, but even if your pursuits are less than academic, you’ll find plenty on offer. Drop your bags at the Middlebury Inn, a stately, four-building brick stay that’s been on the town green since 1827. It's also home to Morgan's Tavern, where Chef John Hessler serves up locally-sourced meals in collaboration with small farmers, artisan cheese makers, and specialty meat suppliers. If you’re still thirsty post-meal, swing by Otter Creek Brewing’s state-of-the-art brewhouse and pub. Along with hoppy drafts, you may even catch a live concert from local VT musicians.

Hugging the shores of Lake Champlain, Shelburne is one of Vermont’s most underrated destinations. The 7,000-resident Burlington suburb may be dwarfed by its northern neighbor, but there’s plenty of reason to stop by. Check in at the Heart of the Village Inn, a Victorian-style B&B that marries antique furnishings with modern amenities. In the area, guests can admire both the Green Mountains (to the east), and the Adirondacks (to the west). For a farm-to-table meal you won’t soon forget, head to the restaurant at Shelburne Farms—a nonprofit organization that advocates sustainable agriculture from their own 1,400-acre working farm. After a meal of Shelburne Farms Pork (with Wapsie Valley polenta, brussel sprouts, stout cabbage, and smoked pumpkin puree), head to the farm store to stock up on maple syrup, farmstead cheddar, and Vermont-made preserves.

Just over the border from Hinsdale, New Hampshire, and only a 10-minute drive from the Massachusetts state line, Brattleboro is a pretty apt picture of greater Vermont’s granola reputation. Get a feel for the artsy town with an indie flick screening at the landmark Latchis Theater—Brattleboro’s one and only cinema. After the show, grab an indulgent dinner at Duo Restaurant. Though owners Keith Arnold and Stephanie Bonin opened their first location (to much success) in Denver, they returned to Bonin’s Vermont hometown to open their second kitchen in 2015, bringing the good people of Brattleboro grass-fed ribeye with kholrabi and potato cheddar gratin, seasonal veggies, and black pepper bordelaise. At the end of the night, retire to 1868 Crosby House, a charming Victorian B&B just a short walk from downtown.

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Quechee is truly one of the Northeast’s ultimate fall sights—leaf peepers and locals will tell you as much. That's when fiery reds, yellows, and oranges highlight the village's tumbling hills and valleys. Though the town’s annual Quechee Hot Air Balloon, Craft & Music Festival—quite possibly the most New England thing to ever exist—doesn’t go off until June, this time of year you can still hop in a wicker basket and take flight across Vermont and New Hampshire. Wherever your itinerary takes you, make sure to include a trip to the tumbling white waters of Quechee Gorge—we suggest viewing it from the bridge along US Route 4—and dinner at the Quechee Inn at Marshland Fine, where a gourmet, locally-sourced three-course menu for two—with wine—will run you only $55. We’re talking mains like grilled salmon with orange zest and ginger-infused honey and Vermont-made bell pepper and smoked mozzarella ravioli in Béchamel sauce.