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The Best Weekend Getaways From New York City

By Claire Volkman, Sarah Buder, and Laura Dannen Redman

Sep 10, 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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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.

Book Now: Sound View Greenport, from $325 per night, expedia.com; Harborfront Inn at Greenport, from $289 per night, expedia.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 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.

Book Now: The Graham & Co., from $137 per night, expedia.com; Wm Farmer and Sons, from $249 per night, expedia.com

Where to eat

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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 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. 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.

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

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.

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.)

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

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.

Book Now: Delamar Greenwich Harbor, from $196 per night, expedia.com

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.

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.

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

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, to include current information. Products we write about are independently vetted and recommended by our editors. AFAR may earn a commission if you buy through our links, which helps support our independent publication.

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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