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The Best Weekend Getaways From New York City

By Claire Volkman

02.21.19

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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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New York City’s cramped subways and crowded sidewalks can take a toll on even the most dedicated city dwellers. For those yearning for a weekend getaway filled with quiet nature walks, visits to local art galleries, and fresh seafood dinners served in waterfront settings, these East Coast escapes provide the respite needed to recharge and relax—all reachable from Manhattan within five hours by train or by car.

In New York State . . .

Family-run wineries, orchards, farms, and seafood shacks characterize Long Island’s North Fork.
Stay low-key on Long Island’s North Fork
Travel time: Approximately three hours by train from Penn Station

With its local wineries, bucolic pastures, farm-to-table food scene, and oyster-abundant coast, Long Island’s North Fork feels worlds away from New York City. In reality, though, the sweet seaside region is approximately 90 miles from Manhattan. 

The peninsula’s largest town, Greenport, 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 features elegant interors inspired by modernist beach homes and is located on a long seaside stretch just a short distance from downtown. Rent a bike on-property and head toward the 19th-century village’s main avenue to peruse vintage clothes, vinyl records, and antique home furnishings 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 dinner at Barba Bianca, a waterfront restaurant situated right on the harbor with a seasonal menu that boasts coastal-Italian delicacies.

Of course, a weekend on the North Fork isn’t complete without some beach time and winetasting. Long Island’s terroir has drawn comparisons to France’s Bordeaux region and the Napa Valley in California because the wine countries sit on approximately the same latitude. Spend an afternoon exploring vineyards along the Long Island Wine Trail, such as Kontokosta Winery (the North Fork’s only waterfront winery, located in Greenport) and Castello di Borghese Vineyard and Winerythe region’s oldest vineyard. Charter a boat with Peconic Water Sports and spend the day on the bay, or hop the ferry from downtown Greenport and relax beachside 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.)

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

Head to the Hudson Valley

Travel time: Approximately two hours by car via Taconic State Parkway

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For New Yorkers, the rolling hills and the 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 river are buzzing with creative energy. 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 warrants a detour, and in Hudson, don’t miss the regularly changing à la carte menu from James Beard Award–winner Zak Pelaccio at Fish & Game, a hyper-local restaurant housed in a former blacksmith shop. 

In recent years, a number of boutique hotels, stylish vintage shops, and straight-out-of-Brooklyn restaurants have popped up across the area 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 museum housed in a former Nabisco box printing factory. And those interested in spending the full weekend outdoors should pass through Phoenicia, where popular day-hikes to Hunter Mountain and Kaaterskill Falls typically culminate in an all-American feast at Phoenicia Diner, a 1960s establishment that’s been restored (and the menu spruced up) for modern enjoyment.

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 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.

The Adirondack Mountains are home to more than 2,000 lakes and ponds.
Lodge lakeside in the Adirondacks
Travel time: Approximately 4.5 hours by car via Taconic State Parkway

With the everyday hustle and bustle of life in the concrete jungle, it’s easy to forget that a six-million-acre state park—larger than Yellowstone, Everglades, Glacier, and Grand Canyon national parks combined—can be reached in just under a five-hour drive 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. 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 strenous summit climbs up the Adirondack High Peaks.

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.

Outside state lines . . .

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

Browse art in the Berkshires, Massachussetts

Travel time: Approximately 3.5 hours by car via Taconic State Parkway

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 art and music thanks to a rush of entrepreneurs transforming the region’s formerly derelict buildings into contemporary galleries and accommodations.

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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 the nearby Mount Greylock and traverse hiking trails that lead to the highest point in Massachussetts.

Rest your head at TOURISTS, a sleek, eco-friendly lodge opened last year by John Stirratt (the bassist with the Chicago alternative rock group Wilco) in North Adams’s previously rundown Redwood Motel.

Greenwich boasts four beaches on the Long Island Sound: Greenwich Point, Byram Beach, Island Beach (Little Captain’s Island), and Great Captain’s Island.
Glam it up in Greenwich, Connecticut
Travel time: Approximately one hour by train from Grand Central Terminal

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 and upscale restaurants), but unlike Manhattan, Greenwich’s hot spots are set among the lush landscapes and relaxing vibe of coastal Connecticut. 

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

Public street art in Philadelphia is so widespread that the city has been nicknamed “the mural capital of the United States.”
Parade through the streets of Philadelphia
Travel time: Approximately 1.5 hours by train from Penn Station

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.

For history lovers, there’s no end to the landmarks and significant buildings on offer in Philadelphia, 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 1700s. It’s also 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 mouthwatering desserts. Or book a table at top-rated Philly restaurants such as Laurel in East Passunk or Fork in Old City.

Museum enthusiasts should definitely plan to visit the Philadelphia Museum of Art, but the jewel in Philly’s cultural crown is undoubtedly in 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 February 20, 2019, to include current information.

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