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New Windsor, New York

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

  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.5
    6.05 mi / 1516 ft gain
    At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...
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  • Dingmans Ferry, Pennsylvania

    Explore George W Child's Park

    4.0
    1.4 mi / 144 ft gain
    Once parked, enter the trailhead and follow the trail down Dingmans Creek to the first set of falls. Try taking pictures from off the trail to the right of these falls. Continue on to the second waterfall and again step off the trail to take pictures from the right side of the waterfall, if you d...
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  • Haines Falls, New York

    Kaaterskill Falls

    4.5
    2.57 mi / 719 ft gain
    Although this is a super short hike, it is definitely a tough one! The quick, steep climb is totally worth it once you reach the 260 foot cascade and pool at the end. Hike along the trail, hugging Spruce Creek all the way to the falls. If you hike in the spring, the creek and the falls will be ra...
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  • Elka Park, New York

    Layman's Monument and Kaaterskill Falls

    3.05 mi / 892 ft gain
    Layman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.
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  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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  • Dingmans Ferry, Pennsylvania

    Hike to Indian Ladder Falls Along Hornbecks Creek

    3.5
    2 mi / 400 ft gain
    For some time, the trail was eroded above the first falls on Hornbecks Creek, not allowing hikers to access the creek's upper falls if they were coming upstream from Route 209. I am writing this in June 2017 and that is no longer the case! You can hike from Rt. 209 all the way up the creek to Eme...
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