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The Best Weekend Getaways From New York City

By Claire Volkman, Sarah Buder, and Laura Dannen Redman

Feb 5, 2021

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Just over a two-hour drive from Manhattan, the Catskill Mountains boast approximately 6,000 square miles of pristine mountains, rivers, forest, and parkland.

Photo by Colin D. Young/Shutterstock 

Just over a two-hour drive from Manhattan, the Catskill Mountains boast approximately 6,000 square miles of pristine mountains, rivers, forest, and parkland.

Getting out of the city has never been easier—if only for 36 hours.

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Our travels may be closer to home these days, but that doesn’t make them any less memorable. Looking for a weekend getaway from the greater New York City area? These East Coast escapes provide the respite needed—quiet nature walks, visits to local art galleries, fresh seafood dinners served in waterfront settings—and are all just a tank of gas away from Manhattan.

North Fork, Long Island, NY

Family-run wineries, orchards, farms, and seafood shacks characterize Long Island’s North Fork.

How far is the North Fork from NYC?

Long Island’s North Fork is about two hours by car from Midtown Manhattan or three hours by train from Penn Station.

Why go to the North Fork?

Local wineries. Bucolic pastures. Farm-to-table food scenes. Oysters up and down the coast. The North Fork feels worlds away from the concrete jungle of New York City, though it’s only 90 miles out to the northeastern peninsula.

Where to stay

Make for North Fork's largest town, Greenport, which offers a laid-back alternative to flashier Long Island escapes like Montauk and the Hamptons. Use Sound View Greenport as your base for the weekend—the revamped 1950s motel is now a 55-room waterfront hotel with a private beach, mixing New England modernist with coastal minimalism (think crisp, clean lines everywhere). Its sister property, Harborfront Inn at Greenport, is another family-friendly option.

Where to eat

For lunch, head to Little Creek Oyster Farm & Market to enjoy shuck-your-own oysters, and don’t miss dinner at Barba Bianca, a waterfront restaurant with a seasonal menu of coastal-Italian dishes.

Things to do

Rent a bike on-property at Sound View and head toward Greenport’s main avenue to shop vintage clothes, vinyl records, and antique home decor at superbly curated boutique shops such as the Times Vintage and Lido.

Of course, a weekend on the North Fork isn’t complete without some winetasting. Long Island’s terroir has drawn comparisons to France’s Bordeaux region and the Napa Valley in California because these wine countries share roughly the same latitude. Spend an afternoon exploring vineyards along the Long Island Wine Trail; Kontokosta Winery is the North Fork’s only waterfront winery, located in Greenport, and Castello di Borghese Vineyard and Winery is the region’s oldest vineyard.

To experience the area’s beautiful beaches, charter a boat with Peconic Water Sports and spend the day on the bay, or hop the ferry from downtown Greenport and relax on Shelter Island, a nature-filled refuge between the North and South Forks.

Start planning your trip with this complete guide to the perfect weekend on Long Island’s North Fork.

Hudson Valley, NY

Breakneck Ridge, located along the Hudson River between Beacon and Cold Spring, is a popular (but strenuous) Hudson Valley hike.

How far is the Hudson Valley from NYC?

You can reach the Hudson Valley in about two hours by car via the Taconic State Parkway.

Why go to the Hudson Valley?

For New Yorkers, the rolling hills and dense pine forests of the Hudson Valley offer a welcome escape from the chaos of the city—but the appeal of this beautiful valley lies well beyond its tree-lined hiking trails and inviting swimming holes. The small, post-industrial towns that line the Hudson River are buzzing with creative energy.

Where to stay

The Hudson Valley and Catskill Mountains have so many cozy bed-and-breakfasts and contemporary boutique hotels that the hardest part of planning a trip to the region can be deciding where to sleep. A few of the most ogle-worthy accommodations in the bucolic upstate New York area include the Urban Cowboy Lodge in Big Indian, the DeBruce in Livingston Manor, Scribner’s Catskill Lodge in Hunter, Eastwind Hotel & Bar in Windham, the Graham & Co. in Phoenicia, and Wm Farmer and Sons in Hudson.

Where to eat

The towns of Nyack, Saugerties, Kingston, and Hudson are all known for their antique scenes and selection of award-winning restaurants. In Kingston, the homey Brunette wine bar and Savona’s Trattoria on Broadway warrant a detour, and in Hudson, don’t miss Feast and Floret, the recently reincarnated Fish and Game (which closed permanently in 2020) that’s now an Italian restaurant serving dishes like rigatoncini alla norma and pork ribs with cipollini and Concord grape reduction. Also make time for an all-American feast at Phoenicia Diner, a 1960s establishment that’s been restored (and the menu spruced up) for modern enjoyment. In COVID times, it has social distancing down to an art with an Airstream food truck and picnic tables.

Where to drink

The beer in the region is so. good. West Kill Brewing on a historic 127-acre dairy farm in the Catskills makes the kind of IPAs you want to bring home by the 30-pack. (Call ahead for its beer garden hours.) Woodstock Brewing, right down the street from Phoenicia Diner, has a creative tap list (Baby Dragon pale ale for the win) and treats you like family.

Things to do

In recent years, a number of boutique hotels, stylish vintage shops, and straight-out-of-Brooklyn restaurants have popped up across the Hudson Valley and added to its ever-increasing hip factor. Art-focused travelers should spend a day strolling through shops along Beacon’s Main Street before touring Dia Beacon, a 300,000-square-foot art museum housed in a former Nabisco box printing factory. Farther north, Woodstock makes for a fun afternoon of window shopping and dessert eating (go just for Peace, Love and Cupcakes and Bread Alone). Those interested in spending the full weekend outdoors should pass through Phoenicia, the starting point for popular day hikes to Hunter Mountain and Kaaterskill Falls.

Start planning your trip with this complete guide to the ideal weekend in Hudson, NY.

Adirondacks, NY

The Adirondack Mountains are home to more than 2,000 lakes and ponds.

How far are the Adirondacks from NYC?

You can reach the Adirondacks in about 4.5 hours by car via the Taconic State Parkway.

Why go to the Adirondacks?

With the everyday hustle and bustle of life in the metropolis, it’s easy to forget that a 6-million-acre state park—larger than Yellowstone, the Everglades, Glacier, and Grand Canyon National Parks combined—can be reached in under five hours from Manhattan. The Adirondacks contain state-protected preserves filled with old-growth forests, glistening streams, and sparkling lakes, but because the area isn’t a national park, there’s no entrance fee.

Where to stay

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For a true Adirondack experience, spend the weekend at a historic “Adirondack Great Camp.” During the early 20th century, industrial behemoths of the Gilded Age vacationed in the Adirondack Mountains, where they built mansion-like log cabins decorated with granite fireplaces and furniture crafted from branches. Today, you can stay in a number of these lodges, including the Point, a great camp built by William Avery Rockefeller on 75 acres of Saranac Lake shorefront nearly a century ago, and White Pine Camp, the one-time Summer White House of President Calvin Coolidge. The Point currently has availability in December and January, including dates around the Christmas holiday.

Things to do

Visitors can canoe or kayak on Lake George, a 32-mile-long body of water nicknamed “The Queen of American Lakes” in the heart of the Adirondack Mountains. The state park also has more than 2,000 miles of hiking trails that cater to every skill level, from low-key nature strolls to strenuous summit climbs up the Adirondack High Peaks.

Berkshires, Massachusetts

With more than 200,000 square feet of exhibition space, MASS MoCA is one of the largest centers for contemporary and performing arts in the United States.

How far are the Berkshires from NYC?

You can reach the Berkshires in about 3.5 hours by car via the Taconic State Parkway.

Why go to the Berkshires?

Adventure and art enthusiasts will find their ideal getaway in the Berkshires, a mountainous area in western Massachusetts that, in recent years, has become a Northeastern epicenter of culture thanks to a rush of entrepreneurs transforming the region’s formerly derelict buildings into contemporary galleries and lodging.

Where to stay

Check into Tourists, a sleek, ecofriendly lodge opened in 2018 by John Stirratt (the bassist with the Chicago alt rock group Wilco) in North Adams’s previously rundown Redwood Motel. Note that during COVID, the lodge is open Thursdays through Sundays with a three-night minimum.

Things to do

Stay the weekend in North Adams, a small city near the Vermont state line that’s home to the Massachusetts Museum of Contemporary Art (MASS MoCA), a 19th-century factory mill complex turned modern center for world-class art. Roam more than 2,000 square feet of the museum’s sprawling exhibition space, then head outdoors to nearby Mount Greylock and traverse hiking trails that lead to the highest point in Massachusetts.

Start planning your trip with this complete guide to the perfect weekend in the Berkshires.

Nantucket, Massachusetts

Nantucket isn’t the quickest weekend getaway from New York, but it’s worth the journey.

How far is Nantucket from NYC?

Nantucket is a deceptively long trip by car: a five-hour drive to Hyannis on Cape Cod, where you pick up the high-speed ferry that gets you to Nantucket in an hour. From late April through early December, Tradewind Aviation runs multiple private and scheduled flights a day between Nantucket Memorial Airport and Teterboro, New Jersey; White Plains and the Hamptons, New York; Farmingdale and Boston, Massachusetts; Philadelphia and Washington, D.C. Talk about zero hassle: You arrive 15–30 minutes before your flight and hang out in a private lounge drinking Nantucket beers and eating peanuts. Then you grab one of only nine seats on the Pilatus PC-12 turboprop plane and minutes later, you’re off. It takes about an hour and costs $875. Yeah, not cheap. The price drops significantly if you buy a round-trip booklet of tickets for multiple trips. 

Why go to Nantucket?

To eat (and eat, and eat), buy books, ride a bike to the beach, learn about the whaling industry, fly a kite, and marvel at the iconic 1700s clapboard homes. 

Where to stay

For your first visit, stay within walking distance of Main Street: Historic three-story brick mansion Jared Coffin House has gorgeous new rooms that celebrate several history-making women—among them, abolitionists Anna Gardner and Lucretia Coffin Mott; Greydon House has one of our favorite outdoor terraces, though the new-in-2020 Life House may take that title with its outdoor firepit and relaxed, convivial vibe. Luxurious White Elephant has multiple residences and suites for families, while the Nantucket Hotel and Resort has a terrific pool and kids’ club. 

Where to eat

The Nautilus is on our digital director’s “top meals of all time” list, namely because of its cocktails and fusion menu (Korean and Hawaiian small plates all the way to Szechuan-style dandan noodles and a mind-blowing Peking duck). Its sister restaurant the Gaslight is popular among locals for its low-key setting (picnic tables during COVID) and killer yakitori. Pick up sandwiches from Born and Bread for a beach picnic, or dig into a dish of oysters from Cru while sitting on the waterfront. B-ACK Yard BBQ has a chopped smoked brisket sandwich we’re still thinking about. And lest you think you can leave Nantucket without a full-tilt seafood dinner, make a reservation at Dune

Things to do

Whether or not you’re a history buff, the Whaling Museum is a must-do to learn the basics of Nantucket’s past—the Wampanoag people, notable abolitionists and suffragettes, 19th-century industry and transportation—as well as its legacy in the whaling industry. Kids will be wowed by the giant sperm whale fossil and replica ships, and you’ll leave knowing more than you thought possible about whale blubber. Private and self-guided walking tours of the island’s historic neighborhoods and architecture are also a highlight. 

Nantiucket is also the perfect place to rent a bike—try Young’s Bicycle Shop on Broad Street or Nantucket Bike Shop—and follow any of these recommended bike paths based on your ability. Also, lesson learned the hard way: If you think you can ride eight miles out on a beach cruiser, remember that you also have to ride back.

Greenwich, Connecticut

Greenwich boasts four beaches on the Long Island Sound: Greenwich Point, Byram Beach, Island Beach (Little Captain’s Island), and Great Captain’s Island.

How far is Greenwich from NYC?

You can reach Greenwich in about one hour by train from Grand Central.

Why go to Greenwich?

You’ll find some of the country’s most expensive homes in Greenwich, Connecticut, but that doesn’t mean the average traveler can’t enjoy this town’s beautiful splendor. Commonly noted as the “Gateway to New England,” the affluent community offers many of the cosmopolitan comforts found in New York City (high-end shopping, spas, and upscale restaurants), but unlike Manhattan, Greenwich’s hot spots are set among the lush landscapes and relaxing vibe of coastal Connecticut.

Where to eat

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To channel peak levels of classic New England elegance, don’t leave Greenwich without trying fresh seafood at L’Escale, a palatial waterfront restaurant inside the upscale Delamar Greenwich Harbor hotel.

Things to do

If shopping stays high on your travel agenda, head to the luxury boutiques along the central Greenwich Avenue (nicknamed “the Ave”) and browse the latest trends at stores such as Hermès and Saks. For more laid-back R&R, visit nearby recreational areas like Byram Shore Park and Great Captain’s Island, or head to Greenwich Point Park to enjoy a long sunset stroll alongside the sweeping Long Island Sound.

Mystic, Connecticut

The quaint seaside town of Mystic is about so much more than pizza.

How far is Mystic from NYC?

Mystic is about a three-hour drive, mostly along I-95, from Midtown Manhattan. You can also take an Amtrak Northeast Regional train from Penn Station to Mystic—add an extra 45 minutes to an hour.

Why go to Mystic? 

The pizza! If you’re not obsessed with the 1988 Julia Roberts rom-com focused on Mystic Pizza and set in Mystic itself, you’ll come for the same riverside charm that delighted screenwriter Amy Jones. Historic downtown Mystic looks every part a New England village, picture pretty with clapboard homes and storefronts, colonial-era steeples, and old sea captains’ residences. It’s the kind of family-friendly getaway where you’ll slow down, sip cider from a 19th-century mill, check out the iconic aquarium, and eat. And eat. And eat. 

Where to stay

The Whaler’s Inn has more than 150 years of heritage—one building was the residence of a shipbuilding family in the 1800s, another was an upscale hotel that opened in 1861. Following an elegant renovation in 2018, the present-day Whaler’s Inn feels like a de facto gathering spot for visitors—centrally located in downtown Mystic, with a wraparound porch and big picture windows that serve up a prime view of the river and Bascule Bridge. It also has multiple room configurations that serve families and groups well, including a suite with bunk beds for the kids.

Where to eat

Don’t feel guilty about multiple stops at Sift Bake Shop, co-owned by pastry chef Adam Young, a Food Network “Best Baker in America”—or that you’re chasing the sticky bun with an apple cider doughnut and hot cider a short drive away at B. F. Clyde’s Cider Mill. The last steam-powered cider mill in the United States (c. 1881), B.F. Clyde’s feels like a time warp—shop the all-things-apple market and sample the hard cider.

If you need a break from all the sweet stuff, Grass & Bone (a high-end butcher and restaurant) and Nana’s (organic bakery and pizza) both do amazing lunches—prosciutto sandwiches with shaved cheese at Nana’s and the rotisserie chicken and Massaman Thai curry at Grass & Bone prompted repeat visits (in a two-night stay). Make a reservation at Oyster Club or Shipwright’s Daughter for a fancier dinner out without the kids.

And, of course, a slice or two at memorabilia-heavy Mystic Pizza.

Things to do

Spend a morning puttering around the locally owned shops in downtown Mystic (Trove Men’s Provisions feels like an old-school haberdashery and Hang the Moon focuses on women-made, ecofriendly, and ethical gifts). 

And lest you think we’d leave out some of the more iconic Mystic activities: The Olde Mistick Village is fun for the family, especially the year-round Sofia’s Mystical Christmas shop and Deviant Donuts. (Don’t count how many doughnuts you’ve had on this trip; it’ll haunt you.) Nearby Mystic Aquarium is a standout with beluga whales, sharks, African penguins, seals, sea lions, and more—though we imagine we had you at beluga whales. 

Philadelphia, Pennsylvania

Public street art in Philadelphia is so widespread that the city has been nicknamed “the mural capital of the United States.”

How far is Philadelphia from NYC?

You can reach Philadelphia in about 1.5 hours by train from Penn Station.

Why go to Philadelphia?

It may not seem like much of a “getaway” to travel from one urban destination to another, but the City of Brotherly Love offers plenty of perks for culture-seeking New Yorkers looking to spend a few days in a slightly smaller city.

Where to stay

In 2019, Philly saw a slate of cool new hotel openings, from business-centric stays to more boutique options. Located on the top 12 floors of the Comcast Center, the Four Seasons Hotel Philadelphia has a 60th-floor Sky Lobby with sweeping city views, plus 219 serene guest rooms and restaurants by acclaimed chefs Greg Vernick and Jean-Georges Vongerichten. For something trendier, try The Notary Hotel, which offers luxury lodgings in the former City Hall Annex, or Fitler Club, a private-club-meets-hotel with an unmatched spa.

Where to eat

Philly is an exciting food city, offering dishes well beyond the beloved cheesesteak (although plenty of iconic establishments serve the namesake dish). Sample fine foods in the Reading Terminal Market, where stalls sling everything from cured meats to fresh cheeses and mouth-watering desserts. Or book a table at top-rated Philly restaurants such as Laurel in East Passyunk or Zahav in Society Hill.

Things to do

For history lovers, there’s no end to the landmarks and significant buildings on offer in Philly, such as the iconic Liberty Bell with its infamous crack or Independence Hall, where the Declaration of Independence and the U.S. Constitution were both signed in the late 1700s.

Museum enthusiasts should definitely plan to visit the Philadelphia Museum of Art, but the jewel in Philly’s cultural crown is undoubtedly its vibrant street art scene. Don’t leave the city without taking a Mural Arts Philadelphia tour to view buildings that have been transformed by imaginative murals.

This article originally appeared online in February 2016; it was updated on September 10, 2020, and then again on December 11, 2020, and on February 5, 2021, to include current information. 

Though COVID-19 has stalled many travel plans, AFAR continues to cover the world; even just planning future travel can boost our happiness. Note that, due to the virus, some of the venues above may have reduced hours or may be open only for delivery or takeout. Please check each venue’s website for the latest.

>>Next: The Best Hotels for New York Weekend Getaways

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