Windham, New York

Top Spots in and near Windham

  • 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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  • Cragsmoor, New York

    Sam's Point, Ice Cave Trail, Verkeerderkill Falls

    4.9
    6.99 mi / 1063 ft gain
    Located in Sam's Point Preserve, this hike has three major attractions – panoramic views from Sam's Point, mysterious and chilly Ice Caves, and a knee-weakening perch atop Verkeerderkill Falls. Pay attention to seasonal conditions before making this trip. Spring and early summer are best for see...
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  • Cragsmoor, New York

    Sam's Point Overlook to Ice Cave Trail

    3.47 mi / 584 ft gain
    Sam's Point Overlook to Ice Cave Trail is an out-and-back trail with scenic views near Lake Maratanza located near Ellenville, New York. This trail is dog friendly on-leash. 
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  • Sheffield, Massachusetts

    Race Brook Falls

    4.0
    2.47 mi / 1145 ft gain
    Hiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...
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  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.7
    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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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.5
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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