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

  • Closter, New Jersey

    Alpine White Trail (Stateline Lookout)

    5.0
    3.86 mi / 856 ft gain
    Starting at about 520 feet, the White path takes you along the Stateline Lookout which is a small stone building overlooking the Hudson River. The initial descent is your average hike through the woods and across a couple of wooden bridges until you reach the Giant Steps. The Giant Steps take you...
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  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
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  • Closter, New Jersey

    Hike to Huyler's Landing/ Closter Dock Loop

    4.0
    5.4 mi / 450 ft gain
    The easiest way to access this loop hike is by parking at the Palisades State Park Headquarters.  This is just off exit 2 from the Palisades Interstate Parkway.  Parking here is free and it is a short walk down a road to the Closter Dock Trail.  The Closter Dock Trail is more of a wide fire road ...
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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  • Philipstown, New York

    Indian Brook Falls (CLOSED)

    2.8
    0.59 mi / 157 ft gain
    Indian Brook Falls is CLOSED as of 2022. Learn more at HighlandsCurrent.org. Take a short simple walk to a beautiful waterfall near the Constitution Marsh and Audubon Center. This waterfall is great spot for the whole family to take in its beauty. This is about as short a walk and as little eff...
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  • Ringwood, New Jersey

    Ringwood Manor Trail

    5.0
    3.06 mi / 381.01 ft gain
    On my way to the drive-in, I saw a sign for Ringwood Manor estate and wanted to adventure around. The parking is easy and the property was beautiful! As we walked through the estate, we found: a quaint tree foresta small cemetery with headstones hundreds of years olda river with a small waterf...
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  • Paterson, New Jersey

    Explore the Great Falls of the Passaic River

    3.3
    Getting to the Great Falls of the Passaic River is a relatively straight shot. It is located off exit 57B on Route 80 which is also accessible from highway 287. Parking is located on McBride Avenue across the street from the park's welcome center.Typically during autumn park rangers offer 45 to 1...
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  • New York, New York

    Top of the Rock

    4.2
    There aren't any mountain peaks to summit in New York City, but the view from the top of the Rockefeller Building is the next best thing. You'll have to pay a few bucks ($29 to be exact) and deal with some tourists but you won't regret your decision once you're looking out over one of the most ic...
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  • Weehawken, New Jersey

    Photograph the NYC Skyline from JFK Boulevard East

    The Big Apple. NYC has arguably the best skyline in the world. So, if you are one of the millions of people visiting wouldn't you want to get some photos of the entire skyline to post on social media and show friend & family? Skip the boat and helicopter tour lines (although a cool experience...
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  • New York, New York

    Run the Hudson River Greenway

    4.3
    18 mi / 212 ft gain
    To get in both some sights and a workout, follow the Hudson River Greenway to views of the Statue of Liberty, the Chelsea Piers, and George Washington Bridge, to name a few. This easy-access run is best done in the early morning or early evening, to avoid pedestrian traffic and too much sun. Keep...
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  • Queens, New York

    Gantry Plaza State Park

    5.0
    Nestled along the East River waterfront in Long Island City, Queens, Gantry Plaza State Park offers visitors a breathtaking urban park experience with unparalleled views of the Manhattan skyline. This 4-acre historic waterfront park transforms former industrial land into a stunning green space ...
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  • Brooklyn, New York

    Kingsland Wildflowers

    4.0
    Kingsland Wildflowers is a rooftop meadow located atop Broadway Stages in Brooklyn’s Greenpoint neighborhood, offering 24,000 square feet of native plants like bee balm, purple aster, and wild strawberries. The green space, a collaboration between Alive Structures, New York City Audubon, and the ...
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  • Beacon, New York

    Explore Long Dock and Dennings Point Parks

    4.0
    Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...
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  • Cedar Grove, New Jersey

    Hike at Mills Reservation

    4.7
    2 mi / 200 ft gain
    Mills Reservation is over 150 acres of wooded area located off of Normal Ave. near the Cedar Grove reservoir. Parking space is limited due to the small size but there is another hidden lot towards the back if you make a right out of the parking lot and then the first right turn onto Highland Ave....
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  • Brooklyn, New York

    Domino Park

    This 5-acre public park in Williamsburg, Brooklyn is perfect for soaking up the sun and taking in the city! Picnic on the grass with lunch and your favorite book, or walk along the water and watch the boats pass by with the Manhattan skyline as your backdrop.
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  • New York, New York

    Walk the George Washington Bridge at Sunset

    3.0
    0.9 mi
    Join the thousands of people who cross the GWB each day, but do it by foot! This is an easy walk with beautiful views of the New York City skyline. You will begin seeing signs for the bridge bike path at Ft. Washington St. & E. 177th St., which you follow for a few blocks until you begin asce...
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