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The 20 Coolest Adventures in New York

Montauk Point Lighthouse

2000 New York 27, Montauk, NY 11954
Located in Greenport, Long Island, this National Historic Landmark is more than just the perfect Instagram pic. A $10 admission gets you access to exhibits on wildlife, history, the environment, and surf culture. Be sure to take a dip at Ditch Plains nearby. And, of course, snag that selfie.

Green-Wood Cemetery

500 25th St, Brooklyn, NY 11232
This historic New York City landmark is an important Revolutionary War site, and also the final resting place of famous mobsters, Civil War heroes, New York mayors, Leonard Bernstein, and more.

Van Cortlandt Park

Broadway & Vancortlandt Park S, Bronx, NY 10462
What if we told you that you didn’t have to leave the five boroughs for more than 1,100 acres, 14 miles of trails, AND a house where George Washington slept? "Absurd!," you might say. But allow us to introduce you to Van Cortlandt Park in the Bronx. This trail-laden sanctuary is most definitely part of New York City, but there isn't a skyscraper in sight. 

Brooklyn Bike Park

318 Kent Ave, Brooklyn, NY 11249
Unleash your inner BMX star at under-the-radar Brooklyn Bike Park. Off-road biking in Brooklyn with Manhattan views? Well, that’s just the best of both worlds! It’s $10 for a two-hour session, or free if you prefer to do your BMXing from the viewers box.

The Cloisters

99 Margaret Corbin Dr, New York, NY 10040
Even if the call of 2,000 works of art and medieval architecture isn’t strong enough to lure you to upper Manhattan, perhaps the views over the Hudson River and outdoor gardens will do the trick. Pro tip: visit in Fall for all that bright orange, yellow, and red.

The Ravine, Central Park

New York, NY 10026
Hop the subway to Central Park for a Catskill-style slice of life right in the center of Manhattan. Designers Olmsted and Vaux envisioned this portion of the park as the city’s answer to upstate -- without that bus ride. Bring a picnic, chase a waterfall, and still make it home for dinner.

Yaddo Gardens

312 Union Ave, Saratoga Springs, NY 12866
If you thought Saratoga Springs was all about horses and mansions, check out this artists' community on a 400-acre, ca. 1900 estate. Pretend you're a Jane Austen character while you stroll by sculptures and rose bushes in the company of Saratogans and resident artists.

Gantry Plaza State Park

4-09 47th Rd, Long Island City, NY 11101
Raise your hand if you knew there was a state park within the five boroughs. Anybody? Bueller? Thought so. But this East River-side park, located in Long Island City, has some of the most amazing, unobstructed views of the NYC skyline, grassy knolls, hammocks, and benches. 

Litchfield Villa

95 Prospect Park West, Brooklyn, NY 11215
This 19th-century mansion is perched atop a hill. Why it’s interesting: it’s a creepy building that looks like the Addams Family home and it’s right in Prospect Park. Get ready for some serious urban exploring.

Kayak with Hudson River Recreation

299 Palmer Ave, Sleepy Hollow
Discover the Croton River in Westchester County aboard a kayak or canoe. Rent a kayak by the hour or join one of their organized tours. Hudson River Recreation has four locations: Sleepy Hollow, Tarrytown, and two in Croton-on-Hudson.

You might think you know the city like the back of your hand, but you can always find something new, unexpected, or plain weird (in a good way) on the Modern Trail. Turn any moment into an adventure, and be dressed to impress with Timberland®.


Shawangunk Mountains

Stop at Mohonk Preserve 3197 US-44, Gardiner, NY 12525
Enjoy 88 miles of striking landscape, mountain roads, hairpin turns, farmers markets, and views of the Catskills and Gunks. The Northern Loop of the Shawangunk Mountains Scenic Byway is a must for any road trip junkie looking to get out of New York for even just a few hours. The byway drive starts in New Paltz and is packed with great vistas, food stops, and hiking. Stretch your legs at Mohonk Preserve -- one of New York’s largest nature preserves. 

Sag Harbor Boating

Long Wharf, Sag Harbor, NY 11963
For a cool $800/night you can score a sweet spot aboard the Nomade, a 35-foot sailboat cruising around one of Long Island’s most posh towns. Captain Eric fills your weekend with lobster rolls, swimming, and shooting star-viewing from the deck. 

Staten Island Ferry

South Ferry Terminal, 4 Whitehall Street, New York, NY 10004
Want a totally free way to see the Statue of Liberty, 24/7? Hop a five-mile ride on the Staten Island Ferry and get up close and personal with Lady Liberty (and Manhattan-Staten Island commuters). 

Tentrr in the Catskills

Fleischmanns, NY
Camping is tough for NYC dwellers, because where are we supposed to store all that gear? But with Tentrr, all you have to do is... show up. Tentrr builds fully-equipped campsites on private land, like an antique apple cider orchard. Arrive to find a tent set up along with a CampBox picnic, a camp toilet, and a fire pit with grill and chairs. It's all yours for about $120 per night.

Vernooy Kill Falls

Trails End Rd, Kerhonkson, NY 12446
Drive Route 28, AKA “New York’s Adventure Route,” and hit Vernooy Kill Falls, a beautiful swimming hole tucked into the mountains. The winding road runs from the Catskills up to the Adirondacks, passing the Ashokan Reservoir and cute towns like Woodstock, Phoenicia, and Cooperstown.

Harriman Outdoor Center

200 Breakneck Rd, Haverstraw, NY 10927
Following a major $2 million upgrade in July, Rockland County’s Harriman State Park just debuted the brand-new Harriman Outdoor Center on the banks of the 64-acre Breakneck Pond. The Center serves as a home base for all the activities to be found in New York’s second largest state park, from hiking, paddling, and s’more-ing. The Center also rents out cabins from $96/night, tent platforms and lean-tos, as well as kayaks and canoes.

Brooklyn Heights Promenade

Pierrepont Pl, Brooklyn, NY 11201
One of the best spots to catch the city in all its glory. The Brooklyn Heights Promenade has a full frontal view of Manhattan that looks great at literally any time of day. Grab yourself a front row seat for a Manhattan sunrise, a view over Lady Liberty, and the Brooklyn Bridge. Lined with restaurants, shops, and bars for all your year-round pleasure.

Bear Mountain State Park

3006 Seven Lakes Drive, Tomkins Cove, NY 10986
Nestled in rugged mountains that rise from the Hudson River, this park, a straight shot up the Palisades Parkway, is a grownup’s playground. Check out the playing field, picnic groves, lakes, river fishing, swimming pool, biking, ski trails, and outdoor ice rink. 

Narrow’s Botanical Garden 

7200-7398 Shore Rd Dr, Brooklyn, NY 11209
Sure, you’ve been to the New York Botanical Garden. You’ve probably even been to the Brooklyn Botanical Garden. So if you’re ready for the next off-the-beaten-path botanicals, make your way to South Brooklyn for this five-acre plot of paradise. The volunteer-run plot has mini gardens replete with lilies, butterflies, and roses, as well as drool-worthy views over New York harbor. Oh, it’s also free to visit if that makes any difference.

The Devil’s Path

Prediger Road, Elka Park, NY 12427
To call this trail a “path” is a tad misleading. To align it with the Devil is not. Not at all hyperbole, The Devil’s Path is one of the most challenging day hikes in the Eastern United States. Cut straight up and down between the gaps of four peaks in this park of the Catskills, this trail requires hikers to strap on their serious hiking shoes and traverse the terrain. Not recommended for casual hikers.