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Northeast Vacations: The 9 Cutest Towns For Your Trip

With lighthouse-scattered coasts, bucolic countryside, rich historical ties, and too many quaint villages to count, the Northeast radiates a relaxed energy no other region could hope to replicate. Here, 9 of the cutest towns to check out next time you’re in the neighborhood.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

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Grafton, Vermont

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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Sugar Hill, New Hampshire

Tucked away in New Hampshire’s rugged White Mountains, with stunning scenic views (especially come fall), hole-in-the-wall antique shops, and a population that hovers around just 560, Sugar Hill has all the trappings of a quintessential New England town. Swing by in June to catch the annual Celebration of Lupines, when the reborn blooms blanket Sugar Hill’s countryside in a brilliant display of blues, purples, pinks, and whites. From there, extend your outdoor time with an excursion in neighboring Franconia Notch State Park. Take a dip in Echo Lake, listen to the roaring waters of the Flume Gorge, or take a ride on an 80-person cable car at the Cannon Mountain Aerial Tramway. On a clear day, you can see straight across NH to Maine, Vermont, New York, and even Canada.

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Kayaking in The Berkshires, Massachusetts
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Stockbridge, Massachusetts

In recent years, the Massachusetts Berkshires have been luring more city slickers out of NYC and Boston than ever. Those in search of a picturesque bucolic escape look no further than Stockbridge, a resort town with relative name recognition thanks to famous resident Norman Rockwell. In fact, many visitors make the hike out to the western MA town just to glimpse the largest collection of the prolific artist's work and personal items at the Norman Rockwell Museum. Priceless art aside, it’s also worth spending some downtime at the Berkshire Botanical Garden and window-shopping the bric-a-brac-filled country stores on Historic Main Street. Once you work up an appetite, head 5 minutes down the road to No. Six Depot in West Stockbridge. The rustic small-batch coffee roaster/café/art gallery serves a mean panini (go for the porchetta with truffle aioli, hazelnut gremolata, and lemon-caper aioli) and—of course—the best caffeine fix in town.

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Montpelier, Vermont

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 chevre 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.

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Hudson, New York

Despite being just over two hours outside Manhattan, Hudson feels worlds away. As “Upstate’s Downtown,” the once sleepy, now trendy city is an amalgam of old-world architecture (Federal, Victorian, and Queen Anne), verdant countryside, and lively art and music scenes. If you’re visiting from the city, you have to make good on outdoor options with hikes through the hemlock-forested wilderness of Taconic State Park and Bash Bish Falls (just over the border in MA). When you need to refuel, mosey back into town for a meal in Wm Farmer & Sons’ handsome, modern-meets-vintage dining room (akin to those you’d find in Brooklyn). Once you’ve stuffed your face with cast-iron burgers and smoked brisket on brioche, retire to Rivertown Lodge. Once a two-story movie theater, you’ll easily spot the stylish stay thanks to its enduring marquee. Inside, the aesthetic is just as pleasing as guest rooms are kitted out with custom-built furniture, white oak floors, brass bathroom faucets, and Americana-style accents.

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Frenchtown, New Jersey

Just a 1.5-hour drive from both NYC and Philly, Frenchtown presents an easy weekend getaway that rivals trips to the Poconos and Hudson Valley. Given its size (tiny), the Delaware River gem is shockingly rife with worthwhile restaurants and boutique shops that run the gamut from home decor to fine jewelry. Since you can’t shop on an empty stomach, make a pit stop at the Lovin’ Oven, a farm-to-table eatery that calls a converted manufacturing warehouse home. On Wednesday’s, they serve a three-course “Welcome Home” dinner full of comfort foods (both traditional and modified) like fish and chips, Nashville fried chicken, and vegan sloppy joes. Post-meal, it's time to peruse eclectic titles at The Book Garden. The indie shop sets up its shelves inside a 19th-century Victorian home on Bridge Street. Pro-tip: if you're looking for a cookbook, head straight for the kitchen.

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Bristol, Rhode Island

Bestowed with the nickname “America’s Most Patriotic Town,” colonial-era Bristol has been proudly hosting the oldest, continuous Fourth of July celebration in the US since they threw their first shindig in 1777. Today, the annual affair includes outdoor concerts, soapbox races, an elaborate parade down Hope Street, and more, but you’ll still find plenty to see and do should your visit fall outside of July. Historical sites are a dime a dozen in this neck of the woods. Spend an afternoon at the Blithewold Mansion, Gardens, and Arboretum a 45-room, heirloom-filled estate that sits on 33 garden-framed acres overlooking Narragansett Bay, and plan time for a visit to Linden Place, as well. If the historic house museum has you feeling some sort of déjà vu, it’s likely you saw its on-screen debut in Robert Redford and Mia Farrow’s The Great Gatsby.

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Mystic, Connecticut

This destination may no longer be under wraps, but the maritime village of Mystic is still a top-notch option for those looking to relax in the Northeast. Nearly equidistance between NYC and Boston, the quaint community is brimming with B&Bs, seaside restaurants, and a world-class aquarium. Drop your bags at Spicer Mansion, a romantic, clapboard inn with only eight lavish guest rooms (think: high ceilings, four-poster beds, and antique-inspired furnishings). From there, it’s time to explore the historic downtown for small mom-and-pop shops and a slice of surprisingly good pizza from the one and only Mystic Pizza (be prepared for lots of Julia Roberts kitsch).

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Castine, Maine

In midcoast Maine, on a peninsula in Penobscot Bay, you’ll find one of the state’s oldest communities: Castine. Rich in seafaring tradition, the harbor town is home to the Maine Maritime Academy, and, perhaps, it’s most easily recognizable feature, the stone Dice Head Light. For classic Maine accommodations, the seaside Pentagoet Inn has you covered. The three-story, turreted Queen Anne Victorian is all about old-fashioned details: vintage lithographs, period antiques, clawfoot tubs, and intricately carved headboards—and its location is ideal, putting you within reach of countless art galleries, flea markets, seasonal fairs, and more. Just a minute down the block, MarKel’s Bakehouse is a must when it comes time to snack. Cinnamon buns, sweet breads, scones, and to-go sandwiches all vie for attention, but once you’ve picked something sweet, retreat back to the inn to relax on the wraparound porch where wicker rockers afford guests stunning views of the bay.

What to Wear in the Northeast

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