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The Best Weekend Getaways From New York City

By Claire Volkman

May 19, 2020

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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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Note: While most of the hotels mentioned below are currently open for business, several restaurants are still closed or only open for take-out service. Some stores, wineries, outfitters, museums, and parks are also still closed or only open to a limited number of people at a time. Check individual websites for updates.

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 . . .

North Fork, Long Island

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

How far is the North Fork from NYC?

You can reach the North Fork in approximately three hours by train from Penn Station.

Why go to the North Fork?

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.

Where to stay 

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 interiors inspired by modernist beach homes and is located on a long seaside stretch a short distance from downtown. 

Book Now: From $362 per night, hotels.com

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 situated right on the harbor with a seasonal menu that boasts coastal-Italian delicacies.

What to do 

Rent a bike on-property at Sound View and head toward Greenport’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

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 the wine regions 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 Winery (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

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 approximately 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 

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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.

Book Now: The Graham & Co., from $137 per night, hotels.comWm Farmer and Sons, from $249 per night, hotels.com

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 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. 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.

What 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. And 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.

Adirondacks

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 approximately 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 concrete jungle, it’s easy to forget that a 6-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. 

Where to stay 

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.

What 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.

Outside state lines . . .

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 approximately 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 accommodations.

Where to stay 

Rest your head at Tourists, a sleek, eco-friendly lodge opened in 2018 by John Stirratt (the bassist with the Chicago alt rock group Wilco) in North Adams’s previously rundown Redwood Motel.

What to do 

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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 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.) 

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 approximately 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 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 

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 Harbor hotel. 

Book Now: From $196 per night, hotels.com

What 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.

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 approximately 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 boasts 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. 

Book Now: Four Seasons Hotel Philadelphia, from $553 per night, hotels.com, The Notary Hotel, from $159 per night, hotels.com; Fitler Club, from $473 per night, hotels.com

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.

What 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 May 19, 2020, to include current information.

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

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