Something about hiking in Windham never gets old. Chase mountain views, wander through beautiful forests, or find a peaceful afternoon outdoors—our corner of New York offers trails for every pace. We've rounded up 5 of our local favorites to help you make the most of your next visit here.
Windham High Peak
Distance: 7.6 Miles (Round Trip)
Difficulty: Intermediate-Advanced
Elevation Gain: 1,750 ft
Highlights: Expansive summit views toward the Hudson Valley and Adirondacks.
After a day on the trail, there is nothing better than coming back to relaxing accommodations, comfortable dining, and a place to unwind. Plan a quick escape or a long weekend; Windham offers the perfect balance of outdoor adventure and small-town charm for both.
Book your stay at The Outpost and spend your days exploring everything our mountain town has to offer. Guided Hiking Excursions are the best way to experience the beauty of Windham.