Trails Near Windham, NY | Trailmonger

About trails near Windham, New York

29 named trails lie within about 25 miles of Windham, covering 25.0 miles in total. 29 of them are tagged for hiking and 24 for mountain biking.

The closest is The Windham Path, about 0.4 miles away. 29 of them lie within 10 miles of town. The longest nearby is Elm Ridge Trail, at 3.4 miles. These trails fall in Greene County.

What the trails near Windham are like

By length, 21 are under a mile and 8 run 1 to 5 miles. 2 are loops, ending where they start; the longest is Elm Ridge Trail, at 3.4 miles.

Of the 24 with a difficulty rating, 1 easy and 23 moderate. Of the 29 with measured elevation, Elm Ridge Trail climbs the most, about 665 ft.

All 29 trails, nearest first

The Windham PathHikeMTBGreene County1.9 mi The Dent Loop Extension of the Windham PathHikeGreene County1.4 mi Peak to PeakHikeGreene County0.7 mi North Face TrailHikeMTBGreene County0.9 mi Twin OaksHikeMTBGreene County0.2 mi UphillHikeMTBGreene County0.3 mi West Gauntlet TrailHikeMTBGreene County1.0 mi Big T TrailHikeMTBGreene County0.6 mi The BeeHikeMTBGreene County0.2 mi Berm-OutHikeMTBGreene County0.9 mi Gold Mine TrailHikeMTBGreene County0.9 mi Levitate TrailHikeMTBGreene County1.4 mi Black Bear Hideout TrailHikeMTBGreene County0.3 mi Lollopop TrailHikeMTBGreene County0.2 mi Mid Mountain TrailHikeMTBGreene County1.5 mi Run Noot TrailHikeMTBGreene County0.9 mi East Gauntlet TrailHikeMTBGreene County0.7 mi Outer Loop North TrailHikeMTBGreene County1.0 mi Trail SixHikeMTBGreene County0.1 mi Outer Loop South TrailHikeMTBGreene County1.4 mi Warm-up LoopHikeMTBGreene County1.0 mi Inside Line TrailHikeMTBGreene County0.7 mi Cranberrry Bog TrailHikeMTBGreene County0.9 mi BoomerangHikeMTBGreene County0.2 mi Inside Out TrailHikeMTBGreene County0.2 mi The Knob access roadHikeGreene County0.9 mi Elm Ridge TrailHikeMTBGreene County3.4 mi Walking PathHikeGreene County0.5 mi Long Path Access (Yellow)HikeGreene County0.6 mi

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Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt October 4, 2026.