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Weekend Getaways

Your Fall 2019 Weekend Guide to New England

New England may be all but ignored for three-quarters of the year, but each fall it gets its due recognition as leaf peepers infiltrate every corner of the region’s six tiny states. More than just fiery foliage and quaint villages, Maine, Vermont, Massachusetts, New Hampshire, Connecticut, and Rhode Island have a lot to offer in the way of culinary know-how, boutique stays, and autumnal cocktails. Here, a handful of the venues on our must-see list, as well as our take on what to wear while you’re in the neighborhood (and no—we’re not suggesting a stereotypical North Face fleece).

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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Drifters Wife, Portland, ME

Peter and Orenda Hale’s East Bayside spot is a wine bar first and foremost, but aside from hand-harvested, all natural vino, Brooklyn-esque Drifter’s Wife serves up some mean seafood. The menu changes daily, but you’ll find dishes like black bass topped with watermelon, crème fraîche, and mint, and hake with eggplant, cherry tomatoes, and radicchio.

Craigie on Main, Cambridge, MA

Just across the Charles from Boston, Craigie on Main whips up seasonally-inspired tasting menus with courses like prosciutto-cured yellowfin tuna and roasted local eggplant. Though every dish comes straight from James Beard award-winning chef Tony Maws, his pièce de résistance is the off-menu grass-fed burger, which has enjoyed its unwavering status as one of Boston’s best since it hit the scene in 2009.

Oberlin, Providence, RI

Chef Benjamin Sukle first showcased his fine-dining expertise with intimate, tasting-menu-only Birch. In 2016, he built off of his success there by opening 50-seater Oberlin, a seafood-centric wine bar. Drop by for killer dishes like raw mahi mahi with olive oil and lemon, and potato gnocchi with shellfish and chives.

The Restaurant at Winvian Farm, Morris, CT

The Restaurant at Winvian Farm does the farm-to-table trend one better with seed-to-table dining as they source fresh ingredients from their own organic gardens. Meals here are cozy as they come—think rotating seasonal dishes like Guinea hen tortellini, roasted rabbit, and asparagus salad accompanied by roaring fires in the spot’s candlelit 18th-century dining rooms.

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Cliff House, Cape Neddick, ME

Drink in Atlantic Ocean views from the clifftop perch of this design-led, southern Maine inn. Far from fishing nets and fake lobsters, the influence here is less New England kitsch and more Scandinavian (think fresh white paint, wooden floors, and clean lines). When you’re not parked in front of the fireplace, taking a dip in the heated pool, or enjoying a sumptuous spa treatment, it’s worth the short trip—we’re talking minutes—down to Ogunquit beach.

Wheatleigh, Lenox, MA

Built in 1893, the 16th-century, Florentine palazzo-style Wheatleigh was once the summer cottage of a Count and Countess. Now, rather than hosting Gilded Age parties, the 380-acre estate welcomes guests with cushy rooms, a wine cellar, and an eponymous park designed by Frederick Law Olmstead—the very dude behind NYC’s Central Park.

The Dean, Providence, RI

Check in at this Downcity 52-room boutique and you’ll be treated to fluffy white duvets, modern minimalist fixtures, vintage artwork, and custom ironwork. If you’re down to socialize with other guests, grab an artisanal latte from Bolt Coffee and hang out in the lobby, chat over candlelit cocktails in the Magdalenae Room, or get rowdy with some karaoke at The Boombox.

Mayflower Inn & Spa, Washington, CT

Just two hours out of NYC, this country escape is tucked away on 58 tidy acres of garden and woodland in quiet Washington, Connecticut. With one of New England’s best spas, you’d be sorry to miss out on a treatment between grabbing a locally-sourced regional dish at the Mayflower Dining Room and unwinding in your light-filled romantic room.

Omni Mount Washington Resort, Bretton Woods, NH

When in New Hampshire, work your way upstate to the Omni Mount Washington Resort. The grand dame—which debuted back in 1902—keeps its interiors as cozy as its mountain setting. Expect roaring stone fireplaces, great halls with vaulted ceilings, marble baths, and four poster beds.

Twin Farms, Barnard, VT

When it comes to stays at all-inclusive Twin Farms, whether you opt for a guest room, cottage, private lodge, or farmhouse, you’ll find plush feather beds, down pillows, and perks like complimentary unpacking services and same day laundry. The intimate mountain hideaway—hugged on all sides by wildflower meadows and hardwood forests—is an ideal Vermont base.

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The Wallingford Dram, Kittery, ME

Maine’s cocktail culture got a much needed kickstart when the Wallingford Dram opened up shop in 2015. The Kittery watering hole offers beer and wine, but the five-page cocktail list is where things get interesting. Our pick goes to the Boat Cowboy—a laundry list of a drink that includes bourbon, tequila, all-spice dram, lime, pineapple gomme syrup, bird's eye chili, and bitters.

Eastern Standard, Boston, MA

This buzzy Kenmore Square brasserie and bar has been kicking for more than a decade, but that hasn’t put a damper on its popularity. Whether you settle into a red leather booth or saddle up to the marble bar, you’ll find an extensive cocktail list including fall specialities like previous years' Bodhi Tree, a combo of house-made fig vermouth, Lemon Hart 151 Demerara Rum, and orange. (Stay tuned for this season's updated options.)

The Black Trumpet Bistro & Wine Bar, Portsmouth, NH

If romantic and unassuming is what you’re after, Portsmouth has a few options. First on our list is Black Trumpet, a family-owned brick warehouse turned wine bar that overlooks the city’s historic harbor. Though the multi-page wine list can be distracting, don’t miss international bites from chef Evan Mallett, a James Beard award semifinalist, while you're at it.

The Malted Barley, Westerly and Providence, RI

Craft beer and gourmet pretzels are a combination we’ll never tire of, and when in Rhode Island, low-key Malted Barley knows how to provide. Swing by the OG Westerly locale, or opt for the downtown Providence outpost—either way, regional drafts (and flights), sweet and savory pretzels, and foosball are on the menu.

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Vermont Icelandic Horse Farm, Moretown, VT

Mad River Valley is a New England must-see—especially come autumn when blazing foliage floods the valley and the air is crisp. Take to quaint backroads, sleepy meadows, and Green Mountain slopes on a trail ride atop a shaggy Icelandic horse. Riders of all experience levels can be accommodated.

Mount Washington Cog Railway, Bretton Woods, NH

In 1869, New Hampshire’s Mount Washington Cog Railway made history as the first mountain climbing train in the world. Today, visitors can chug up the mountain on a three-hour, round-trip ride to take in 360 degree views of NH backcountry as it lights up in fiery reds, oranges, and yellows. Don’t forget your camera!

Mohawk Trail, Athol to Williamstown, MA

Running roughly 69 miles from Athol to Williamstown, Massachusetts, the Mohawk is a leaf peeper's dream. Taking Routes 2 and 2A, foliage fiends follow the trail as it runs parallel to the Deerfield River and over the Connecticut River, with astounding views of the Berkshires and Taconic Mountains all the while. Drive cautiously as you might run into a bobcat or black bear, but what's most dangerous is the trail's infamous hairpin turn—Dead Man's Curve.

The Philip Johnson Glass House, New Canaan, CT

Thousands of visitors make the trek out to New Canaan each year to take in architect Philip Johnson’s astounding, 47-acre Glass House estate. Once you’ve admired the simplicity of the all-glass structure, check out the 14 surrounding buildings which utilize quintessential New England stone walls and barn foundations.

Park Loop, Acadia National Park, Mount Desert Island, ME

When it comes to taking in Acadia's best coastal views by car, this scenic 27-mile route is the only way to go. Starting at the Hulls Cove Visitor Center (just off Route 3 on the northern side of the island), the road loops past Sand Beach, Thunder Hole, Otter Cliffs, Jordan Pond, and 1,530-foot Cadillac Mountain—the highest point along the North Atlantic seaboard.

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