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Windham, New York

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

Top Fitness Spots in and near Windham

  • Haines Falls, New York

    Summit North Mountain

    4.5
    6 mi / 855 ft gain
    Have you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills.Parki...
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  • Haines Falls, New York

    Camp at North Lake Campground

    During an unplanned road trip, we arrived at the North/South Lake Campground out of curiosity and without a doubt, it was totally worth the stop! (We only saw North Lake.) To visit this campground, there is a fee for a day pass, unless you had just came from another campground in the Catskills li...
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  • Elka Park, New York

    Backpack the Eastern Half of Devil's Path in the Catskill Mountains

    5.0
    14 mi / 3900 ft gain
    The Eastern half of Devil's Path has four major summits: Indian Head, Twin, Sugarloaf and Plateau. Each summit is a straight climb up and down, then back up to as much as 3,900 ft. There are some sparse sections of level ground, but most is a steep descent uphill or steep slide downhill. Your ...
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  • Gardiner, New York

    Gertrude's Nose

    4.9
    6.97 mi / 919 ft gain
    It would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...
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  • Mount Washington, Massachusetts

    Climb Alander Mountain

    10.6 mi / 2250 ft gain
    Close to the popular Bash Bish Falls in Mount Washington State Forest is this amazing summit and perfect day hike! Witness the corners of Massachusetts, Connecticut, and New York all at once (and from the top of this trail, it connects to Bash Bish if you have the time to spear!) From the Mt. Was...
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  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 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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  • Great Barrington, Massachusetts

    Hike the Lookout Trail in Beartown State Forest

    0.5 mi / 117 ft gain
    If you ever decide to go to the beautiful Beartown State Forest, be sure to enjoy the short but worthy hike to the vista on the Lookout Trail for views that stretches out to the mountains. There are two places to park:  1. From the main entrance of the park, you can get a spot at the lot at Bened...
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  • Great Barrington, Massachusetts

    Hike the Benedict Pond Loop Trail

    5.0
    1.7 mi
    This is no ordinary loop, it's rain forest-like feels with small hills and curves, wooden bridges over marsh, and lookouts over the pond will keep you in awe at every corner! The trail is easy to find and easy to follow. When you park at the boat launch area, follow the blue blazes and trail sign...
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