22 Long Weekend Getaways From Boston

Edited by Brittany Jasnoff

There are 22 weekends left until 2021 is behind us—which means 22 opportunities to hightail it out of town. From New Jersey to Maine, golfing to rock climbing, and everything in between, we’ve rounded up the perfect number of must-do long weekends to take you from the end of summer all the way through New Year’s Eve. So make your reservations and pack your bags: You have 72 hours to recharge. Ready, set, go!

Golfing

Turning Stone Resort Casino

Verona, New York

Drive Time from Boston
4 hours, 30 minutes

When it comes to golf destinations, there’s no question that Turning Stone should be near the top of any player’s bucket list—and luckily, you don’t have to travel far (or stay long) to get your swing at it. Located in the Mohawk Valley just 30 miles east of Syracuse, the property offers more golf than any other resort casino in the country—but for those sweeping open spaces that upstate New York does so well, you’ll want to hit the flagship Tom Fazio–designed Atunyote course, which has hosted the PGA Professional National Championship multiple times. Listen to babbling brooks, take in the gently rolling hills, and follow in the footsteps of the greats while you’re here—Tiger Woods, Matt Kuchar, Steve Flesch, and Camilo Villegas have all played the Atunyote. Once you’ve ticked that off your to-do list, there are still the Shenendoah and Kaluhyat courses—a little more approachable in terms of difficulty but no less impressive when it comes to scenery.

After a day on the links, spend your night unwinding at any of Turning Stone’s many dining and entertainment venues. It’s hard to beat a sunset reservation at TS Steakhouse for dinner. Located atop the resort’s Tower Hotel, the award-­winning restaurant boasts expansive views in every direction. There are several options for sleeping while you’re here, but we suggest the Lodge at Turning Stone, situated away from the casino’s hustle and bustle—and, more important, just steps from the Shenendoah and Kaluhyat courses. —Todd Plummer

3 More Golf Getaways

1
Golf at Bretton Woods
Bretton Woods, New Hampshire

Drive Time from Boston
2 hours, 30 minutes

Turns out the White Mountains aren’t just for skiers: During the warmer months, take your golf game to new heights on the two courses abutting Omni Mount Washington Resort. Start on the Mount Pleasant Course—with just nine challenging holes, it’s a suitable warm-up or an ideal choice if you only have a half day to hit the links. When you’re ready for the main event, book a tee time for the 18-hole Mount Washington Course. Not only are the views of the White Mountains breathtaking (especially timed with fall foliage), but you’ll have at your fingertips everything this iconic Omni—which recently added a new wing—has to offer. Pro tip: Be sure to take advantage of the enormous spa. —T.P.

2
Point Sebago Golf Course
Casco, Maine

Drive Time from Boston
2 hours, 30 minutes

Sparkling lakes, green fields, white birch forests, and perhaps the occasional black bear or two—Maine’s picture-perfect Point Sebago Golf Course is considered one of the finest in the state. Set on 500 manicured acres, this par-72 18-holer is suitable for golfers of all levels. Opt for the Stay & Play package with Point Sebago Resort and you can even snag a well-appointed vacation home for as little as $125 a night—or go for the true Maine experience and book a campsite from just $55. —T.P.

3
Ocean Edge Golf Club
Brewster

Drive Time from Boston
1 hour, 45 minutes

Sorry to twist your arm, but you’ll just have to book a room to play here—the Jack Nicklaus–designed course at this popular Lower Cape resort is available only to guests and golf-club members. Once you unpack your clubs, expect complicated doglegs, dramatic elevation changes, and tough approaches. Sure, it’s a challenging course, but when you get to unwind at the 19th hole with a sunset cocktail on the terrace—or better yet, down at the beach bar—it’ll be impossible not to kick back and let loose a little. —T.P.

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Islands

Block Island

Rhode Island

Travel Time from Boston
3 hours

Magical views, gourmet meals, and mopeds: While this island measures only 7 miles long and 3 miles wide, there are more ways than ever to pack a long weekend with beachy fun. First, disembark after the 30-minute high-speed ferry ride from Point Judith in Narragansett and feast your eyes upon the 19th-century Victorian that is the Block Island Beach House. Steps from the dock, the recently revamped hotel debuted 15 new coastal-chic rooms and group-friendly suites this year, plus the island’s only hotel pool. Inside, you’ll find original Block Island artwork in every room; outside, the sprawling covered porch—part of the hotel restaurant, the Surf—hosts weekly clambakes.

Crescent Beach, one of the island’s most picturesque stretches, is a short walk from the hotel, though you’ll want to make sure to rent a bicycle (or a moped) at some point and pedal down to Mohegan Bluffs. There, jaw-dropping seaside cliffs, 141 steps down to the water, and a Gothic Revival–style brick lighthouse circa 1874 await. When it comes time to eat, explorers with an appetite will relish the fresh clam strips and seafood nachos at the Beachead. Those who prefer to rinse off the salt before a night out should reserve a table at Restaurant 1879 at the Atlantic Inn, where you can start with spicy watermelon gazpacho, tuck into citrus-and-white-wine-poached lobster on a bed of squid-ink orecchiette, and finish with the chocolate torte, a duck-fat-infused chocolate cake with peanut butter ganache, candied peanuts, and cardamom Chantilly cream. A sweet ending to a sweet trip, you bet. —Madeline Bilis

3 More Island Getaways

1
Chebeague Island
Maine

Travel Time from Boston
2 hours, 15 minutes

One of the most easily accessible Maine islands (it’s just 15 minutes from Yarmouth via a painless ferry ride), Chebeague still feels
like a throwback to simpler times. Exhibit A: The little town’s only hotel, Chebeague Island Inn, is the stuff of New England summer dreams, with a wraparound porch, a great room complete with a fireplace and board games, and a restaurant that receives its fresh lobster direct from local fishermen each day. Have the hotel shuttle you up—or borrow a house bike for the 3-mile journey—to the scenic, secluded Indian Point Beach, where you’re likely to have the sandy expanse all to yourself. —T.P

2
Île d’Orléans
Quebec, Canada*

Travel Time from Boston
6 hours, 30 minutes

Natural beauty—not to mention succulent produce—abounds in this storybook setting smack in the middle of the St. Lawrence River, just a short ride over the bridge from Quebec City. Start by picking your own raspberries, strawberries, and blueberries at a farm called L’Arc-en-ciel du Paradis, or the Rainbow of Paradise. As the sun sets, venture to Isle de Bacchus, one of the area’s beloved vineyards, to sip on a sweet glass of ice wine. While the island is dotted with adorable inns, the ultra-cozy La Suite du Quai offers proximity to the lavender fields at the botanical garden La Seigneurie de l’Île d’Orléans (pictured below). —M.B.

3
Shelter Island
New York

Travel Time from Boston
4 hours

A hop, skip, and two quick ferry rides away from New London via Orient, the Northeast’s best-kept secret is more than worth the trip for the sprawling beaches, exceptional food and wine, and rambling nature trails with none of the crowds (or turned-up noses) you’ll find elsewhere on Long Island’s East End. Drop your bags at the Chequit, a fully restored 150-year-old inn, take a stroll through the 2,350-acre Mashomack Preserve, then head straight to Sunset Beach in time for waterfront drinks. Dinner at Vine Street Café is a must thanks to an Ina Garten–endorsed Bolognese that’s one of the best you’ll find this side of Italy. —T.P.

*Be sure to check travel restrictions before booking your trip.

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Off-the-Grid Resorts

The Sagamore Resort

Bolton Landing, New York

Drive Time from Boston
3 hours, 45 minutes

How’s this for off-grid? Built in 1883, this sprawling Victorian-style resort occupies its own private island on Lake George. Don’t worry, you can still drive there via a small bridge—but a guard house at the entrance ensures that pesky day-trippers are kept at bay. Once you ditch your car and check in, there’s really no reason to cross back over to the real world. This is, after all, the kind of old-school place that has just about everything you want in a getaway: rooms with private patios featuring Adirondack rocking chairs; eight restaurants and bars ranging from fine dining to a casual pub; indoor and outdoor pools and hot tubs; an 18-hole golf course; a spa and salon offering everything from sports massages to mani-pedis; and splendid Adirondacks views all around. You can choose to do it all, or you can choose to simply sit back in a lounge chair and soak up the sun bouncing off the water.

While there’s plenty for grownups to enjoy, the Sagamore is the kind of magical escape the little ones will love exploring, too—including at an adorable rec center where they can play Wiffle Ball and mini golf and meet new friends at the kids’ club. Once everyone has chosen their respective adventure, the whole family can reunite in time for a sunset cruise aboard the hotel’s touring boat, which offers scenic rides around Lake George. —T.P.

3 More Off-the-Grid Getaways

1
Twin Farms
Barnard, Vermont

Drive Time from Boston
2 hours, 45 minutes

Could there be anything more romantic than a private mountaintop dinner for two—and only two? At Twin Farms, spread over 300 acres of rolling farmland and forest, you can savor locally grown greens and crispy pork belly in a refurbished ski gondola situated atop the property’s private ski slope. The new dining experience isn’t the only thing you’ll love about this luxe all-inclusive. Whether you’re craving some hard-to-find Heady Topper beer for your room’s mini fridge, an afternoon of guided fly-fishing on one of the farm’s private streams, or a picnic-style lunch down by Copper Pond, your every wish is Twin Farms’ command. —T.P.

2
Chatwal Lodge

White Lake, New York

Drive Time from Boston
4 hours, 30 minutes

The sister to one of Manhattan’s top boutique properties, the soon-to-open Chatwal Lodge is less like a hotel and more like your fanciest friend’s country estate in the Catskills. Accommodations will include 10 suites with private patios overlooking the placid Toronto Reservoir Lake; an 850-square-foot glamping tent; and—if you really want to splurge—a treehouse floating 25 feet above the ground. You’ll have your pick of unplugged activities while you’re here, too, from kayaking to picnicking on the grounds. —T.P.

3
Miraval Berkshires
Lenox

Drive Time from Boston
2 hours

Think of this recently opened, all-inclusive Berkshires retreat as a break-glass-in-case-of-emergency option if you need a serious wellness reset. Check in and choose from demonstrations and lectures offered by world-renowned nutritionists, spiritual healers, and more, plus more than 20 different types of yoga and meditation classes. Then unwind in the sublime spa or with a meal emphasizing local ingredients and healthy, mindful eating. You’ll be saying namaste in no time. —T.P.

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Adventures

Surfing

York Beach, Maine

Drive Time from Boston
1 hour, 15 minutes

New England is well known among the surfing community for its gnarly winter storm swells—in fact, newbies are often surprised at just how many shops and instructors there are everywhere from Newburyport up to Portland, Maine. For those just getting their feet wet, though, summer and fall in York Beach—with its sandy shores and gentle waves—is the perfect time to learn. Start the day with a latte at Central Bean & Bakery, where you’re likely to encounter other surfers fueling up before paddling out. Once you’re ready to try your luck hanging 10, the experts at Liquid Dreams Surf Shop will get you started on the right course, whether that’s hooking you up with rentals, setting up a lesson, or helping you select your first board and wetsuit for purchase.

The area has been beloved by water-sports enthusiasts and families for decades, but it’s about to get a whole lot cooler thanks to the mod rooms and surfer vibes of the brand-new York Beach Surf Club, a completely fresh take on what was once a dusty motel. The new owners redid the space in what they call “Scandi-Maine” design, but the heart and soul of the property is a heated saline pool complete with food and beverage service right to your lounger. After spending the day paddling the waves—or even providing moral support from the comfort of terra firma—it’s definitely the place to be. —T.P.

3 More Daring Getaways

1
Rock Climbing
New Paltz, New York

Drive Time from Boston
3 hours, 30 minutes

Known as one of the best climbing spots in the U.S., Shawangunk Ridge (affectionately called “The Gunks”) is an enormous bedrock ridge that stretches from New Jersey to just north of the town of New Paltz in Ulster County, New York. Whether you’re a beginner looking for a rock-climbing 101 course or a seasoned pro in need of a guide to brush up on your skills, the experienced instructors at Eastern Mountain Sports Schools offer a range of courses as well as private and family group lessons. When it’s time for a little R&R after a full day of climbing, check into the tony Mohonk Mountain House, where the award-winning spa is well versed in tailoring treatments to tired arms and legs. —T.P.

2
Hunting and Clay Shooting
Richmond, Rhode Island

Drive Time from Boston
1 hour, 30 minutes

Close your eyes and picture a place with 3,500 unspoiled acres teeming with pheasants and wild turkeys. No, we’re not talking about the northern woods of New Hampshire or Maine; we’re talking about the Preserve, a Rhode Island hotel, residential development, and sporting club that offers a bucolic escape from the demands of city life just 80 miles from Boston. Get comfortable inside one of the luxurious cabins, suites, or multi-bedroom homes available for rent—or check out the new safari-style glamping tent and cigar experience on offer this fall—then let the property’s guides set you up for clay shooting, continental hunting, or even a pheasant tower shoot. —T.P.

3
Exploring
Mount Desert Island, Maine

Drive Time from Boston
4 hours, 30 minutes

The Pine Tree State is about more than just lobsters and wild-blueberry everything. With the highest coastal mountains on the Eastern Seaboard, there are enough trails in Acadia National Park to entice any adventurer—don’t miss hiking or driving Cadillac Mountain at sunrise (pictured)—not to mention plenty of gentle carriage roads for less-daring explorers. And while outdoor excursions always take center stage this time of year, the area still has plenty of creature comforts, whether you prefer staying in a West Elm–furnished glamping tent at the brand-new Under Canvas, or at the recently renovated Claremont Hotel, where the waterfront Batson Fish Camp restaurant offers panoramic views over one of the only fjords in North America. —T.P.

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Kids

The Jersey Shore

Drive Time from Boston
5 hours

Forget the fist-pumping crowds of beer-slinging, sun-worshiping twentysomethings you’ve seen on TV. Though in recent years this stretch of coastline has gotten the reputation as a party spot thanks to a certain MTV show, the area is actually an ideal place for kids, with plenty of boardwalks featuring carnival-style rides and amusements and all the old-fashioned shore fun (think: taffy, fudge, and soft-serve custard) that families here have been enjoying for generations, plus a few new surprises along the way.

The region is also a lot bigger than you might think, stretching from the New York border all the way south to Cape May, and each town has its own unique vibe. On the southern end, the Wildwoods’ 38-block boardwalk offers more than 100 rides spread out over three piers, not to mention two water parks steps from the sand. Of course, there’s plenty for the adults to love, too, including the recently renovated Shore House in North Wildwood, built on the foundation of a classic 1960s motel but beautifully updated for the 21st century. Nearby Ocean City also boasts rides, go-carts, and all the pizza and fries you can eat on its bustling boards. Mornings, meanwhile, are for pedaling a four-wheeled surrey as the salt air whips your hair.

Though you won’t find a ride-heavy boardwalk in revitalized Asbury Park, farther north, you will find the Asbury Splash Park, mini golf, and the Silverball Arcade just off the beach—plus a recently opened boutique hotel, the Asbury Ocean Club, with a stunning pool overlooking the water. If the kids are still begging to hop on a Ferris wheel, Casino Pier in Seaside Heights—yes, the one made famous by Snooki and JWoww—is only a 45-minute drive, and packed with enough thrills, including the brand-new Xolo Loca roller coaster, for a whole day of fun in the sun. —Brittany Jasnoff

2 More Kids’ Getaways

1
Winnetu Oceanside Resort
Martha’s Vineyard

Travel Time from Boston
2 hours, 30 minutes

Owners Mark and Gwenn Snider believe that everyone should feel like a kid on vacation—which probably explains why their plush resort, just a short stroll from South Beach in Katama—has everything under the sun that families need to let loose and relax, quite literally. A complimentary day program for children featuring treasure hunts, art projects, and nearby field trips through early September? You got it. An on-site babysitter at the Dunes restaurant, so parents can unwind al fresco with a cocktail at sunset? Of course. Lemonade, cookies, and antique fire-truck or jitney rides every day starting at 2 p.m. for all ages? Sign us up. —B.J.

2
Legoland
Goshen, New York

Drive Time from Boston
3 hours, 45 minutes

Any adult who has stepped on a piece of Lego in bare feet can attest to children’s abiding love for this classic toy. Now, the whole clan can experience its infinite wonders at the massive Legoland Resort that opened this summer in upstate New York. The $500 million theme park took five years to build and features rides and attractions based on the brand’s most popular toys. The Legoland Hotel has themed rooms ranging from pirates to ninjas, and beyond rides like the Dragon’s Apprentice mini coaster and DJ’s Dizzy Disco Spin, the interactive complex lets kids feel like they’re actually a part of the action. Shoes most definitely recommended. —Jonathan Soroff

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Food & Drink

Hudson

New York

Drive Time from Boston
3 hours

During the pandemic, hordes of die-hard New Yorkers fled their fair city—but on the bright side, that means a food and drink revolution has flourished in the Hudson Valley, a place with the history and charm of New England but a distinct flavor all its own. It’s entirely possible to spend several days—or weeks, in fact—zigzagging through the region, but a single weekend in the town of Hudson is a great introduction to what you’ll find in the area: farm stands spilling over with seasonal produce and homemade baked goods; every sort of restaurant, from farm-to-table favorites to high-brow fine dining; and an abundance of craft breweries.

Make the exquisitely hip Maker Hotel your home base as you make your rounds through the town’s greatest hits, from pork-belly bao at Hudson Food Studio, to Wm. Farmer and Sons’ mouthwatering cast-iron foie gras with pistachio butter and rhubarb jam, to the cod cheeks with spring vegetables at Le Perche. Of course, it wouldn’t be a visit to Hudson without sampling the award-winning Tainted Senorita coffee stout at Hudson Brewing Co., the best place in town to ply locals for their favorite places to eat and drink. When you’re ready to turn in for the evening, head back to the hotel—but not before stopping by the Lounge for a nightcap. After all, it’s hard to think of a more quintessentially Hudson experience than a round of bourbon smashes inside the restored 19th-century carriage
house. —T.P.

2 More Gourmet Getaways

1
Providence
Rhode Island

Drive Time from Boston
1 hour

As if Providence didn’t offer enough mouthwatering reasons for an Italy-inspired culinary road trip—hot spots Enoteca Umberto and Pane e Vino among our favorites—the new Beatrice hotel, a boutique property that’s set to open in September, boasts the first outpost of the Cipriani restaurant empire in New England. The hotel is named after developer and former mayor Joseph Paolino’s mother, and the sleek wood, white, and gray rooftop restaurant, Bellini (pictured above), pays homage to the cocktail invented at the Cipriani family’s most iconic property, Harry’s Bar in Venice. Like the rest of the Cipriani eateries, this one will feature regional specialties, making it a quick trip to Italy, senza passport. —J.S.

2
Montreal
Quebec, Canada*

Drive Time from Boston
5 hours

When you can’t spare the time or expense for a proper European escape, a weekend in this Canadian gastronomic capital is a more-than-worthy replacement. Thanks to its diverse population, Montreal is in the midst of a culinary revolution, making eating your way through the city more exciting than ever. Start by booking a room at the Hotel William Gray, Old Montreal’s most adorable boutique hotel. From there the sky’s the limit: Try the Argentinian-Mediterranean fusion at Beba (pictured below); Ethiopian at East Africa Restaurant; grilled Portuguese fare at Ma Poule Mouillée; classic French bistro dishes at L’Express; and, of course, poutine at the kitschy Gibeau Orange Julep. Walk it off with a stroll through the cobblestone streets of Old Montreal and listen to passerby speaking French for an experience that’s nothing short of transporting. —T.P.

*Be sure to check travel restrictions before booking your trip.

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