Local Trails


Stewart State Forest
Managed by New York State Department of Conservation
Location: Ridge Road, New Windsor, 12553 ~ Orange County, NY
5,264 acres – Trails, some marked, some not; throughout.Directions:From Rt. 17K west heading to the town of Montgomery shortly past the historical marker for the Site of Cobden Mansion (just before Stone Castle Road on the right) turn left onto Ridge Road and head over US 84 on a bridge; park in the parking area on the left.

There is another parking area off Rt. 207 – west of Sculley’s.

Winding Hills Park
Managed by Orange County Parks
Location: Old Route 17KMontgomery, 12549 • 845-457-4918 ~ Orange County, NY
Snowmobile Trail is marked and follows the perimeter of the park. Directions:From Rt. 17K west go through the town of Montgomery. Just after Kaisertown Road (on the left) you’ll see a sign for the Park on the right. Bear right onto Old 17K and right into the Park.

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