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Explore Trails - with  people on trail

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

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.

Trailhead: Route 23

Time: 4-5 Hours

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Black Dome

Black Dome & Thomas Cole

Distance: 7.5 Miles (Loop)

Difficulty: Challenging

Elevation Gain: ~2,625 ft

Highlights: Summit view with spectacular viewpoints and enjoyable scenery between peaks.

Trailhead: Batavia Kill Trail

Time: 5-6 Hours

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Kaaterskill Falls

Katterskill Falls

Distance: 1.8 Miles (Round Trip)

Difficulty: Easy-Moderate

Elevation Gain: 390 ft

Highlights: 260-foot, two-tier waterfall; viewing platforms and stone staircases

Trailhead: Multiple; Laurel House Road (Upper Lot)

Time: 1-2 Hours

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Acra Point

 

Acra Point & Burnt Knob

Distance: 4.8 Miles (Round Trip)

Difficulty: Moderate

Elevation Gain: 1,220 ft

Highlights: Mountain views, streams, footbridges, stunning forest.

Trailhead: Batavia Kill Parking Area

Time: 2.5-3 Hours

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Overlook

 

Overlook Mountain Peak

Distance: 4.7 Miles (Round Trip)

Difficulty: Moderate

Elevation Gain: 1,390 ft

Highlights: Gravel trail with steady incline, old ruins, fire tower, great views.

Trailhead: Meads Mountain Rd

Time: 3-4 Hours

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A Place to Unwind

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.

 

PLAN YOUR STAY

Windham Mountain Club - One Trail at a Time Windham Mountain Club