Best trails in Windham, New York

868 Reviews
Looking for a great trail near Windham, New York? AllTrails has 7 great hiking trails, trail running trails, dogs leash trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Catskill Park or John Boyd Thacher State Park, we've got you covered. You'll also find some great local park options, like Kaaterskill Wild Forest or Indian Head Wilderness. Ready for some activity? There are 3 moderate trails in Windham ranging from 5.9 to 7.4 miles and from 1,771 to 3,526 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Windham, New York
Top trails (7)
#1 - Windham High Peak via Elm Ridge Trail
Windham-Blackhead Range Wilderness
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(311)
Length: 5.9 mi • Est. 3 h 23 m
#2 - Windham Trail
Elm Ridge Wild Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(259)
Length: 6.7 mi • Est. 3 h 53 m
#3 - Windham High Peak via Black Dome Range Trailhead
Windham-Blackhead Range Wilderness
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(76)
Length: 7.4 mi • Est. 4 h 24 m
#4 - The Windham Path
Catskill Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(103)
Length: 2.4 mi • Est. 1 h 2 m
#5 - Escarpment Trail: HWY 23 to North/South Lake
Catskill Park
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(42)
Length: 18.4 mi • Est. 10 h 55 m
#6 - Inside Line Trail and Outer Loop North Trails
Elm Ridge Wild Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(37)
Length: 3 mi • Est. 1 h 24 m
#7 - Cave Mountain
Catskill Park
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(16)
Length: 5.2 mi • Est. 2 h 5 m
The actual trail to Cave Mtn.’s peak goes off to the East at 1.5 miles in. You’ll walk with the resort’s ATV roads for a few hundred feet and the hiking foot path will be to your right (South) into the woods. You should see a sign for the “Peak to Peak” path and a green emblem with a hiker on the trees.Show more