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Chestertown, New York

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

Top Hiking Spots in and near Chestertown

  • Inlet, New York

    Hike Rocky Mountain Summit

    5.0
    1 mi / 448 ft gain
    This half-mile, steep hike to the 2225 foot summit of Rocky Mountain has some great views of Fourth Lake and the surrounding area from it's open summit. Simply follow the steep, well worn trail (and yellow DEC discs) to the summit. The round trip of this hike is one mile, with an elevation gain ...
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