Looking for a weekend getaway from the greater New York City area? Lucky for you, there are countless appealing destinations reachable via a quick train ride or road trip from the Big Apple, all with plenty of activities, hotels, and restaurants to fill a weekend. These East Coast escapes provide the respite needed—quiet nature walks, visits to local art galleries, a day trip here and there, fresh seafood dinners served in waterfront settings—and are all only a tank of gas away from Manhattan and Brooklyn. Read on for nine of our top picks for the best weekend getaways from New York City.
The laid-back beach town of Montauk is an ideal place for a relaxing getaway.
Photo by Lyndsey Matthews
1. Montauk, New York
- Distance: 2.5 by car or 3.5 hours by train from Penn Station
- Best for: A laid-back beach getaway
A relaxed alternative to upscale beach towns in the Hamptons just to the west, Montauk is best known for its surf breaks, like the ones at Ditch Plains and the Terrace. So pack your swimsuit, sign up for a surfing lesson, and plan on eating as much seafood as you can.
What to do in Montauk
For breakfast, head to Montauk Bake Shoppe for its famous jelly croissant (coffee snobs can get their needs met at Left Hand Coffee). Don’t miss the sunset views dinner at Duryea’s, a classic seafood shack right on the water overlooking Fort Pond Bay. Close out the night by drinking a beer or two with locals at Shagwong Tavern, a dive bar in the center of the village that’s been open since 1936.
Between meals, take a surf lesson or rent gear at Engstrom Surf, located at Marram Hotel. Beginners are in safe hands with the Engstrom siblings—Leif, Ariel, and Lexi are all world-renowned surfers—who will have you paddling out and attempting to catch waves in no time. If you prefer being on the water instead of in it, you can book a private charter for groups of anywhere from 2 to 100 passengers with Catamaran Mon Tiki for a sunset cruise departing from Star Island in Lake Montauk.
Where to stay in Montauk
Check in to Marram, a quiet beachfront hotel located right on the Terrace surf break. Open-air communal spaces—like courtyard firepits with complimentary s’mores and a guests-only pool deck overlooking the Atlantic—are ideal for those who want to spend the most time outside this summer.
Just off the traffic circle at the center of town—and still 100 feet from the ocean—Daunt’s Albatross has been operated by multiple generations of the Daunt family since 1977. The 24 guest rooms come with kitchenettes perfect for week-long stays as well as Parachute linens and towels, custom-made knotty alder furniture, indigo-hued textiles as art, and sleek flagstone floors. As part of a year-long redesign, the Daunt family acquired the restaurant across the street, the Bird, which now serves breakfast, lunch, and dinner seven days a week.
Read more: The perfect weekend in Montauk
Breakneck Ridge, located along the Hudson River between Beacon and Cold Spring, is a popular (but strenuous) Hudson Valley hike.
Photo by Jeff P./ Flickr
2. Hudson Valley, New York
- Distance: two hours by car via the Taconic State Parkway
- Best for: Scenic hikes and small towns filled with creative energy
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, postindustrial towns that line the Hudson River are buzzing with creative energy that make it an excellent choice for a weekend trip.
What to do in the Hudson Valley
The towns of Nyack, Saugerties, Kingston, and Hudson are all known for their antique scenes and selection of award-winning eateries and cafés. 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 reincarnated Fish and Game (which closed 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.
Absolutely do not sleep on the breweries, some of which host live music now and then. 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. 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.
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. 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).
Where to stay in the Hudson Valley
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, Wm Farmer and Sons in Hudson, and the brand-new (as of 2022) Wildflower Farms in Gardiner, which was on AFAR’s list of the best new hotels in 2022.
Read more:
- The ideal weekend in Hudson, New York
- Hotel review: Wildflower Farms Offers a High-End Escape for Nature-Starved New Yorkers
Family-run wineries, orchards, farms, and seafood shacks characterize Long Island’s North Fork.
Photo by Sarah Buder
3. North Fork, Long Island, New York
- Distance: two hours by car; three hours by train from Penn Station
- Best for: Wine, food, and ocean vistas
Local wineries. Bucolic pastures. Farm-to-table food scenes. Oysters and lobster rolls 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.
What to do in the North Fork
A weekend on the North Fork isn’t complete without some winetasting. Long Island’s terroir has drawn comparisons to French wines—specifically France’s Bordeaux region—and 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. 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. For lunch, head to Little Creek Oyster Farm & Market to enjoy shuck-your-own oysters, and don’t miss lunch or dinner at Salumeria Sarto, a tiny, 16-seat Italian restaurant on the waterfront that’s a Salumeria by day and Osteria by night.
Where to stay in the North Fork
Make for North Fork’s largest town, Greenport, which offers a laid-back alternative to flashier Long Island escapes like 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.
Read more: The perfect weekend on Long Island’s North Fork
Be sure to visit Seventh Lake while in the Adirondacks—especially during the summertime.
Photo by Michelle Heimerman
4. Adirondacks, New York
- Distance: 4.5 hours by car via the Taconic State Parkway
- Best for: Exploring a state park filled with old-growth forests
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 within the boundaries of New York State, just under five hours from Manhattan. The Adirondacks contain state-protected preserves filled with old-growth forests, waterfalls, glistening streams, and sparkling lakes, but because the area isn’t a national park, there’s no entrance fee.
What to do in the Adirondacks
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.
Where to stay in the Adirondacks
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.
For an art and culture-filled getaway, head to the Berkshires, with a stay at the hotel Tourists (left) and a visit to museum MASS MoCA (right).
Photos by Lyndsey Matthews
5. Berkshires, Massachusetts
- Distance: 3.5 hours by car via the Taconic State Parkway
- Best for: An art-filled escape
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.
What to do in the Berkshires
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.
Where to stay in the Berkshires
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.
Read more:
- The perfect weekend in the Berkshires
- Hotel review: How Wilco’s Bassist and His Friends Turned a Berkshires Motel Into Tourists, a Dream Summer Getaway
Nantucket isn’t the quickest weekend getaway from New York, but it’s worth the journey.
Photo by Shutterstock
6. Nantucket, Massachusetts
- Distance: six hours by car and ferry
- Best for: Eating-fresh seafood
Nantucket is an ideal destination for anyone who wants to eat (and eat, and eat), buy books, ride a bike to the beach, learn about the whaling industry, fly a kite, all while marveling at the iconic 1700s clapboard homes.
What to do in Nantucket
Head to The Nautilus, which has a location in Nantucket and one in Boston, for its stand-out 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, killer yakitori, and live music. 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.
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. Private and self-guided walking tours of the island’s historic neighborhoods and architecture are also a highlight. Nantucket 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.
Where to stay in Nantucket
Near Main Street, historic three-story brick mansion Jared Coffin House has gorgeous rooms that celebrate history-making women, like abolitionists Anna Gardner and Lucretia Coffin Mott. Greydon House has one of our favorite outdoor terraces though boutique hotel, Life House is a close contender 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.
Getting to Nantucket
From New York City, it’s 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 scheduled flights between Nantucket Memorial Airport and Teterboro, New Jersey; and White Plains, New York. (Private charters are available between Nantucket and Farmingdale and Boston, Philadelphia, and Washington, D.C.) It takes about an hour and costs $875.
Greenwich boasts four beaches on the Long Island Sound: Greenwich Point, Byram Beach, Island Beach (Little Captain’s Island), and Great Captain’s Island.
Photo by James Kirkikis/Shutterstock
7. Greenwich, Connecticut
- Distance: one hour by train from Grand Central
- Best for: A relaxing coastal getaway
Only an hour by train from Manhattan, Greenwich, Connecticut, is commonly noted as the “Gateway to New England.” For weekend visitors, the affluent community offers many of the cosmopolitan comforts found in New York City (high-end shopping, spas, and upscale restaurants), but unlike the city, Greenwich’s hot spots are set among the green landscapes and relaxing vibe of coastal Connecticut.
What to do in Greenwich
Don’t leave Greenwich without trying fresh seafood at L’Escale, a palatial waterfront restaurant inside the upscale hotel, Delamar Greenwich Harbor. 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.
Where to stay in Greenwich
Book a room in the waterside Delamar Greenwich Harbor hotel; some guest rooms have balconies overlooking the harbor. Or check-in to a luxurious suite at the J House Greenwich. Both hotels are excellent options for a wellness moment, with full-service spas on site.
The quaint seaside town of Mystic is about so much more than pizza.
Photo by Shutterstock
8. Mystic, Connecticut
- Distance: three hours by car; four hours by Amtrak from Penn Station
- Best for: Pizza, beer, and learning about the town’s nautical history
Even if you’re not obsessed with the 1988 Julia Roberts rom-com focused on Mystic Pizza and set in Mystic itself, 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.
What to do in Mystic
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. Make a reservation at Oyster Club or Shipwright’s Daughter for a fancier dinner out without the kids. And, of course, eat a slice or two at memorabilia-heavy Mystic Pizza.
Spend a morning exploring 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). Don’t sleep on the town’s most iconic activities: The Olde Mistick Village is fun for the family, especially the year-round Sofia’s Mystical Christmas shop and Deviant Donuts. 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.
Where to stay in Mystic
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 overlooking the river. It also has family-friendly rooms, including a suite with bunk beds for the kids.
Public street art in Philadelphia is so widespread that the city has been nicknamed “the mural capital of the United States.”
Photo by Jon Bilous/Shutterstock
9. Philadelphia, Pennsylvania
- Distance: 1.5 hours by train from Penn Station
- Best for: Culture, history, and food in a smaller city
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.
What to do in Philadelphia
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.
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.
Where to stay in Philadelphia
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. 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.
This article originally appeared online in 2016; it was most recently updated in August 2023, to include current information. Additional reporting by Lyndsey Matthews and Erika Owen.
