Westchester County, New York

Looking for the best chillin in Westchester County? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Westchester County. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Chillin Spots in and near Westchester County

  • West Milford, New Jersey

    Hike the Terrace Pond North - South Loop

    10.7 mi / 1200 ft gain
    From Warwick Road, parking at the northernmost road side parking area, cross the road, and the Terrace Pond North trail (marked with blue blazes) begins as a steady climb until you gain a ridge that offers some great views for several miles. Eventually, you'll reach a power line where you turn ri...
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  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • Brooklyn, New York

    Climb Outdoors at DUMBO Boulders (CLOSED)

    5.0
    Practice bouldering at North America's largest outdoor rock climbing gym after work. Of course you aren't climbing mountains, but at least the view of the East River isn't too shabby! Enter at the corner of Adams St. and John St. and see the Manhattan Bridge above you. To your left is the new ...
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  • Brooklyn, New York

    Photograph Manhattan Bridge from Washington Street NYC

    4.7
    Located in DUMBO this is seen as one of of the prime photography spots in NYC for good reason. Off the intersection of Washington Street and Water Street is a perfect view of the Manhattan Bridge sandwiched between two buildings. If you want to take it one step further you are able to get a close...
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  • Brooklyn, New York

    Photograph the Brooklyn Bridge

    4.8
    Escaping the hustle and bustle of the city doesn't always require actually leaving the city. Hanging out next to the East River and focusing on photographing the Brooklyn Bridge can be just what you need to clear your head and get your fix for some outdoors time. This is a great spot to practice ...
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  • New York, New York

    Explore the South Street Seaport

    5.0
    Get a feel for what New York was like in the 19th century at the Seaport! The Seaport boasts some of the oldest buildings and architecture in Manhattan, and the area continues to bustle today. The Seaport borders the Financial District and the East River - so there are lots of wonderful sights to...
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  • Brooklyn, New York

    Brooklyn Bridge Park

    4.0
    The Brooklyn Bridge Park spans over a mile of waterfront and is an awesome location for being active or just relaxing outdoors without leaving the city. There is a ton of grassy space to set up a picnic and watch the sunset and many other options for fun - basketball courts, a carousel, roller sk...
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  • New York, New York

    Battery Park

    4.5
    Located at the Battery, the southern tip of Manhattan Island in New York City, facing New York Harbor. The Battery is named for the artillery batteries that were positioned there in the city's early years to protect the settlement behind them. There's also multiple transportation going on underne...
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  • Warwick, New York

    Enjoy a Film at the Historic Warwick Drive-In

    Take a trip back in time at the Warwick Drive-In and watch a feature film on the big screen. The Drive-In shows movies just in theaters and older films with three different screens / options to chose from. The theater sells tickets for both one movie and for double features, i.e. watch two movies...
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  • 89 Van Orden Road, New Jersey

    Hike the Hank's Pond Loop

    7 mi / 500 ft gain
    Hank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road.  I hiked from the south on this trip.  Follow the wide trail known as Hank's East trail marked with white blazes.  Soon you will reach a trail c...
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  • Staten Island, New York

    Sunrise and Sunset from the Staten Island Ferry

    5.0
    The Staten Island Ferry is a passenger ferry that runs between the boroughs of Manhattan and Staten Island. From the deck of the ferry, you will have a perfect view of The Statue of Liberty and Ellis Island. You'll see the skyscrapers and bridges of Lower Manhattan receding as you pull away and c...
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  • Brooklyn, New York

    Camp at Floyd Bennett Field

    Brooklyn isn't just for the urban and trendy, its also for the people who love getting outside! Located just past the hustle and bustle of Brooklyn, Floyd Bennett Field is a National Recreation Area that features an Aviator Sports & Event Center (this was formerly an important NYC airport), t...
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  • Dover Plains, New York

    Hike Dover's Stone Church

    4.5
    Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
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  • Gardiner, New York

    Hike the Overcliff - Undercliff Road Loop

    5.3 mi / 350 ft gain
    From the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk.  The trail connects the parking lot to the Overcliff Road/Undercliff Road junction.  The loop can be done in either direction.  I turned left on the Overcliff Road.  This takes you behind...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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  • Frankford, New Jersey

    Picnic at the Sunrise Mountain Pavilion

    This pavilion is one of the key features along the New Jersey section of the Appalachian Trail. There is a parking lot a very short hike part way down the mountain, but I recommend backpacking in from a different area to take in more of the beauty of the trail, mountains, and views in this area. ...
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