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Cragsmoor, New York

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

Top Hiking Spots in and near Cragsmoor

  • Briarcliff Manor, New York

    Hike Kate Kennard Trail

    1.8 mi / 140 ft gain
    If you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...
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  • Rockaway, New Jersey

    Hike the Timberbrook Pond - Riley's Rise Loop

    5 mi / 500 ft gain
    The trailhead parking is at the end of Timberbrook Road, before the road enters Camp Winnebago (Boy Scouts). I hiked this in a clockwise directions starting on the Timberbrook Trail (yellow markers).  After about 1 mile the trail ends at a junction with the Four Birds Trail (white markers).  Turn...
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  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
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  • Greentown, Pennsylvania

    Camp at Rustic Bear Wallow Cabins

    Rustic Bear Wallow Cabins are the ideal compromise between going camping and staying home. Enjoy an intimate connection with the natural landscape of Pennsylvania, including two lakes and the Pocono Plateau of Promised Land State Park. Explore the rich landscape, enjoy the water, and come home to...
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  • Greentown, Pennsylvania

    Conservation Island Nature Trail

    1.08 mi / 36 ft gain
    Conservation Island Nature Trail is a loop trail that is good for all skill levels located near Greentown, Pennsylvania.
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