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Fire Island lighthouse
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Labor Day weekend getaways from NYC

Bid farewell to summer with one of these Labor Day getaways from NYC

Written by
Tolly Wright
,
Hannah Streck
&
Shaye Weaver
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A three day weekend is the perfect opportunity to bid farewell to summer. While we’re sad for summer to end, Labor Day gives us a chance to celebrate with one last hurrah. It’s never too soon to start planning an amazing Labor Day getaway from NYC, so check out these options, from relaxing to adventurous.

While there are plenty of day trips from NYC that can scratch the itch, the long weekend is enough time to squeeze in a weekend getaway. Looking for some culture? Head to the Hamptons. Partial to the outdoors? The Adirondacks are for you. If you’re more of a shorebird, consider Wildwood or Fire Island. Sure, you could hit up the best beaches in NYC or salute the summer at an outdoor bar or beer garden, but to squeeze every last drop out of summer, start planning one of these Labor Day getaways from NYC today.

RECOMMENDED: Full guide to Labor Day in NYC

Labor Day getaways from NYC

Catch waves and live music in Montauk
Photograph: Shutterstock

1. Catch waves and live music in Montauk

120 miles, 3hrs by car or LIRR

Head East and don’t stop until you reach the tip of the Hamptons, where the ritzy clubs and high-fashioned vacationers give way to lifetime native fisherman and surfers who quit New York to chase the area’s big waves. If you’re hoping to hang ten yourself, spend your mornings at Ditch Plains, a beach where you'll be among many longboarders and have access to tasty seasonal food trucks. Afterward, spend your night dining over fresh seafood at 668 The Gig Shack, hit a Lynn's Hula Hut for some tiki drinks, and say goodbye to summer with live music as the sun sets behind a pond at the hip Surf Lodge.

  • Things to do

100 miles, 2hrs 30mins by car or various times by LIRR

If the warm weather or sun is threatening to run away before the (unofficial) end of summer, a weekend in the Hamptons is still worth the schlep to Long Island. If you want to skip the beautiful white sands of Cooper Beach and East Hampton’s award-winning Main Beach for amazing cultural activities, check out the Pollock-Krasner House and Studio. Here, you can see where famed artists Jackson Pollock and his wife Lee Krasner spent their days in peaceful seclusion creating Modern art pieces, including some by Pollock that are still exemplified as the best of Abstract Expressionism.

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Enjoy the wilderness in the Adirondacks/Lake George
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3. Enjoy the wilderness in the Adirondacks/Lake George

200 miles, 3hrs 20mins by car

For a true breath of fresh air, ditch New York City for the simple life in upstate New York. After you spend a full day dedicated to theWild Walk, a system of wooden bridges that snakes through the Adirondack Park as a “High Line of the Forest,” which offers stunning views of the trees and wildlife, check out the area’s fun low-key events. Try out some of the area's best wine at the Adirondack Winery Lake George Tasting Room in Lake George or Head to Fort Ticonderoga to explore its gardens, learn its history, and hike its Carillon Battlefield trail with views of Lake Champlain and Vermont's Green Mountains.

Relax on the beach at Fire Island
Photograph: Shutterstock

4. Relax on the beach at Fire Island

60 miles, 2hrs 15mins by car

It can take a bit of planning to get to this car-free summer oasis, but if you haven’t been, hop aboard the first ferry you can for the perfect fun-in-the-sun destination. Catching those last rays of summer sun on one of the well-maintained beaches, for a 3-day beach party. Get into the groove at a gay bar called Sip-n-Twirl or relax with a cocktail with a waterfront view at Cherry's On The Bay.

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Party by the sea at Wildwood, New Jersey
Photograph: Cinzia Reale-Castello

5. Party by the sea at Wildwood, New Jersey

155 miles, 2hrs 30mins by car

Forget what you think you know about the Jersey Shore from the late but memorable MTV series—this spot is the real deal. The whole weekend is jam-packed with ways to get your America on, from the Naval Air Station Wildwood Aviation Museum's Labor Day Weekend AirFest to the Boardwalk Craft Fair. Don’t forget to leave time for exploring the historic boardwalk—there’s plenty of shops and rides waiting for you.

Escape to the mountains in artsy Beacon, NY
Photograph: Richard Barnes

6. Escape to the mountains in artsy Beacon, NY

1hr 30mins from NYC by car

Beacon is steeped in history (Beacon Mountain, the tallest point of the Hudson Highlands, played a significant role in the American Revolution), but besides its storied past, it’s also packed with modern-day culture. The city has an arty, indie spirit that attracts…arty, indie people. You'll want to check out the former Nabisco box-printing facility on the banks of the Hudson, called Dia:Beacon, which holds art collections from the 1960s to the present. Exhibitions meld with works on long-term view from artists including Walter De Maria and Dan Flavin. Take a guided tour (free with admission) every Saturday and Sunday at 12:30pm and 2pm to get the best overview. 

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Taste exceptional wine in the Finger Lakes
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8. Taste exceptional wine in the Finger Lakes

250 miles, 4hrs 30mins by car

Sure, Long Island has plenty of wineries, but in upstate New York you get a refreshing glass while appreciating the hills and blue lakes of this quiet region of the state. Sip some of the town’s best Riesling offerings while overlooking a lake from the Ravines Wine Cellars’ tasting room, or the green Adirondack chairs at Sheldrake Point Winery. While you’re in the area, designate a non-boozy day and take advantage of the canoeing and kayaking opportunities, or maybe take a dip under a waterfall.

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Indulge in quaint New Hope, PA
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9. Indulge in quaint New Hope, PA

1hr 45mins from NYC by car

New Hope is Bucks County’s jewel, unhurried and unassuming, with indie boutiques (onetime East Village staple Love Saves the Day), seasonal-focused eateries (Stella) and forget-all-your-troubles B&Bs galore. Between hopping to different quaint spots, be sure to get back to nature. We suggest cruising on a rented bike down the Delaware Canal towpath. New Hope has stunning woodlands and meadows throughout, which you can appreciate at Bowman’s Hill Wildflower Preserve.

See the art of the Berkshires, MA
Photograph: Shutterstock

10. See the art of the Berkshires, MA

150 miles, 2hrs 45mins by car

If the weather’s nice, it’s imperative that you go white water rafting and hike the gorgeous Monument Mountain or speed down a zipline through a thick forest, but if you’re all natured-out, have no fear. This region of Massachusetts is full of amazing art opportunities. Check out true Americana art at the Norman Rockwell Museum, the fantastic architecture and magnificent collection of the Clark Art Institute and the largest collection of contemporary visual and performing arts in the country at MASS MoCa.

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Dine and shop in Greenwich, CT
Photograph: Shutterstock/James K

11. Dine and shop in Greenwich, CT

1hr 30mins from NYC

Greenwich may bring to mind finance commuteres and tennis courts and, yes, it certainly has a lot of those, but it's also a gorgeous community of 60,000 that still has a small-town feel. And it's only an hour out of the city by train! With plenty of beaches, harbors, restaurants and sweet neighborhood to explore, it's a gentle escape from the city—and you don't have to be a financier to visit. Spend a leisurely afternoon browsing the many shops, eateries and bars along Greenwich Avenue. In the evening, do not miss a meal at Back 40 Kitchen, a farm-to-table restaurant that's worth the trip to Greenwich on its own. The interior is warm and homey, with wood paneling, industrial lights and only several tables in the entire space. Chef Ian Vest showcases delicious dishes such as as deviled eggs, pappardelle and mint stracciatella ice cream. The meal is every bit as good, and far less expensive, than the last gourmet meal you had in the city. 

Shop till you drop in Hudson, NY
Photograph: Courtesy CC/Flickr/Teri Tynes

12. Shop till you drop in Hudson, NY

110 miles, 2hrs by car or 2hrs 20mins by train

The walkable and bike-friendly town of Hudson only has 6,000 residents, but it’s an upstate treasure that is easily accessible to and from the city. With 300 historic buildings, including many with exceptional architectural elements, and over 50 antique stores, this spot is perfect for a full day of moseying. Start at a local café like Rev Coffee & Tea before heading down Warren Street for a slew of galleries displaying works by contemporary locals, oil paintings and antiquities from around the world over. Once you’re inspired, drop by any one of the numerous vintage and antique stores to search for new furniture, jewelry and decorative items to fit your taste. Before you leave, check out the historic lighthouse and the killer views of the Hudson River.

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