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The Best Hiking in New Windsor

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

Top hiking spots in and near New Windsor

  • Beacon, New York

    Dennings Point via Madam Brett Park

    3.07 mi / 128 ft gain
    Dennings Point via Madam Brett Park is a loop trail that takes you by a river located near Beacon, New York.
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  • Beacon, New York

    Dennings Point and Klara Sauer Trail

    4.87 mi / 233 ft gain
    Dennings Point and Klara Sauer Trail is an out-and-back trail that takes you by a waterfall located near Beacon, New York.
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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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  • Beacon, New York

    Sugarloaf Mountain via Wilkinson Memorial Trail

    3.7
    2.15 mi / 820 ft gain
    Trail is currently closed. Sugarloaf Mountain is part of the Hudson Highlands State Park, along with Breakneck Ridge, Bull Hill, and Mt Beacon. Though the views are just as impressive as its sister trails, it is never as crowded and it's one of my favorite spots in all the Hudson Valley. Parking...
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  • Beacon, New York

    Sunset Point - South Beacon Mountain Loop

    4.0
    8.92 mi / 2470 ft gain
    This loop hike form the Notch Trail northern trailhead on Route 9D.  There is enough parking at this trailhead for about 5-6 cars.  The Notch Trail is identified with blue trail markers.  It is well maintained and plenty of markers to guide your way.  This is important because there are m...
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  • Beacon, New York

    Breakneck, Sugarloaf Mountain and Cold Spring

    10 mi / 2520 ft gain
    Breakneck, Sugarloaf Mountain and Cold Spring is a point-to-point trail that takes you by a lake located near Cornwall-on-Hudson, New York.
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  • Cornwall-on-Hudson, New York

    Hike the Stillman - Bluebird Loop

    5.4 mi / 1200 ft gain
    This loop hike starts at the northern trailhead of the park where the Stillman Trail begins.  The parking area has enough space for only 6 or 7 cars.  Start off on a wide maintained carriage road.  After about a half mile, the Stillman Trail (yellow markers) breaks of to the left.  However, stay ...
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  • Beacon, New York

    Beacon Fire Tower via Breakneck Ridge, Wilkinson and Notch Trails

    9.44 mi / 2100 ft gain
    Beacon Fire Tower via Breakneck Ridge, Wilkinson and Notch Trails is a loop trail that provides a good opportunity to view wildlife located near Cornwall-on-Hudson, New York.
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  • Beacon, New York

    Breakneck Ridge, Breakneck Bypass, Wilkinson Trail Loop

    3.02 mi / 1142 ft gain
    Breakneck Ridge, Breakneck Bypass, Wilkinson Trail Loop is a loop trail that takes you by a waterfall located near Cold Spring, New York.
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  • Beacon, New York

    Breakneck Ridge, Undercliff, Green Blazes, and Brook Trail Loop

    2.64 mi / 1063 ft gain
    Breakneck Ridge, Undercliff, Green Blazes, and Brook Trail Loop is a loop trail that takes you through a nice forest located near Cornwall-on-Hudson, New York.
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  • Beacon, New York

    Breakneck Ridge, Notch, Brook Loop

    4.14 mi / 1306 ft gain
    Breakneck Ridge, Notch, Brook Loop is a loop trail that takes you through a nice forest located near Beacon, New York.
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  • Beacon, New York

    South Beacon Mountain via Breakneck Ridge and Wilkinson Memorial Trail

    8.92 mi / 2470 ft gain
    South Beacon Mountain via Breakneck Ridge and Wilkinson Memorial Trail is a loop trail that takes you by a river located near Cornwall-on-Hudson, New York.
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  • Beacon, New York

    Breakneck Ridge, Undercliff, and Brook Trail Loop

    2.5 mi / 1024 ft gain
    Breakneck Ridge, Undercliff, and Brook Trail Loop is a loop trail that provides a good opportunity to view wildlife located near Fishkill, New York.
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  • Cold Spring, New York

    Breakneck Ridge Trail to Casino Trail

    5.85 mi / 1946 ft gain
    Breakneck Ridge Trail to Casino Trail is a point-to-point trail that takes you by a river located near Cold Spring, New York.
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  • Cold Spring, New York

    Sugarloaf Mountain and Breakneck Ridge Loop

    4.7
    4.33 mi / 1562 ft gain
    The Breakneck Ridge to Sugar Loaf Loop gives rise to various bypasses that offer hikers moderate to advanced terrain and multiple rock scrambles. The loop entails a total elevation gain of 1,670 feet and a total distance of 5.5 miles. The start of the trail begins at the (white blazes) at the no...
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  • Cold Spring, New York

    Breakneck Ridge Loop

    5.0
    5.91 mi / 1526 ft gain
    This short but steep loop hike in Hudson Highlands State Park offers multiple panoramic views of the Hudson River along the way. Please note that only experienced hikers should attempt this route – although the hike seems short, the elevation gain and steep rocky scrambles offer serious technical...
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