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The Best Hiking in Woodbury

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

Top hiking spots in and near Woodbury

  • Woodbury, New York

    Schunnemunk Mountain via Red Trail to Jessup Trail

    5.41 mi / 1010 ft gain
    Schunnemunk Mountain via Red Trail to Jessup Trail is an out-and-back trail that provides a good opportunity to view wildlife located near Highland Mills, New York.
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  • Cornwall, New York

    Old Mineral Springs Trail

    3.71 mi / 564 ft gain
    Old Mineral Springs Trail is an out-and-back trail that takes you by a waterfall located near Cornwall, New York.
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  • Mountainville, New York

    Schunemunk Mountain via Dark Hollow and Sweet Clover Loop

    6.37 mi / 1509 ft gain
    Schunemunk Mountain via Dark Hollow and Sweet Clover Loop is a loop trail where you may see local wildlife located near Cornwall, New York.
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  • New Windsor, New York

    Hike Jessup/West Ridge Loop via the Sweet Clover Trail

    10 mi / 1700 ft gain
    Schunnemunk Mountain State Park is one of my favorite parks.  It offers many trails and possibilities for different loops.  The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions.This hike starts at the Taylor Road parki...
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  • Mountainville, New York

    Schunemunk Mountain via Jessup Trail Loop

    8.1 mi / 1617 ft gain
    Schunemunk Mountain via Jessup Trail Loop is a loop trail that takes you by a waterfall located near New Windsor, New York.
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  • Mountainville, New York

    Schunemunk Sweet Clover Loop

    4.89 mi / 1253 ft gain
    Schunemunk Sweet Clover Loop is a loop trail that takes you by a river located near New Windsor, New York.
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  • Monroe, New York

    Hike the Jessup/Highlands/Long Path Trails

    7.8 mi / 500 ft gain
    This trails starts at a small park in Woodbury called Gonzaga Park.  Closed from mid-November to April, you are still able to park just outside the gate if that is the time of year you are hiking.  Three different trail names share this path.  The Jessup trail starts/end at Gonzaga Park and trave...
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  • Cornwall, New York

    Split Rock, Chattfield, Spy Rock, and Eagle Cliff Loop

    6.28 mi / 1001 ft gain
    Split Rock, Chattfield, Spy Rock, and Eagle Cliff Loop is a loop trail that takes you by a lake located near Cornwall, New York.
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  • Cornwall, New York

    Sackett, Sutherland Road, and Split Rock Loop

    4.05 mi / 554 ft gain
    Sackett, Sutherland Road, and Split Rock Loop is a loop trail that takes you by a lake located near Cornwall, New York.
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  • Cornwall, New York

    Black Rock, Hill of Pines, Rattlesnake Hill, and Sutherland Pond Loop

    7.73 mi / 1056 ft gain
    Black Rock, Hill of Pines, Rattlesnake Hill, and Sutherland Pond Loop is a loop trail that takes you by a lake located near Cornwall, New York.
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  • Cornwall, New York

    Otterkill Trail

    4.48 mi / 476 ft gain
    Otterkill Trail is an out-and-back trail that takes you by a waterfall located near Salisbury Mills, New York.
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  • Cornwall, New York

    Schunemunk Mountain via Western Ridge Trail Loop

    7.47 mi / 1588 ft gain
    Schunemunk Mountain via Western Ridge Trail Loop is a loop trail that takes you by a river located near Salisbury Mills, New York.
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  • Tomkins Cove, New York

    Torrey Memorial via New Loop

    1.87 mi / 305 ft gain
    Torrey Memorial via New Loop is a loop trail that takes you by a lake located near Bear Mountain, New York.
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  • Tomkins Cove, New York

    Trans Harriman Via Longpath

    15.13 mi / 1640 ft gain
    Trans Harriman Via Longpath is a point-to-point trail that takes you through a nice forest located near Highland Falls, New York.
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  • Woodbury, New York

    Black Mountain and Owl Lake Loop

    7.14 mi / 1047 ft gain
    Black Mountain and Owl Lake Loop is a loop trail that takes you by a lake located near Harriman, New York.
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  • Highland Falls, New York

    Popolopen Torne

    4.5
    1.18 mi / 531 ft gain
    Popolopen Torne is a hidden gem in the Hudson Valley, a surprisingly unknown trail with a beautiful payoff and a far deeper meaning. A short hike to the top puts you at the foot of a memorial to those who have served their country, a pile of painted rocks carried up by those who want to pay their...
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