Windham area has great hiking spots.
Windham High Peak from Rt 23 - 7.50 mile trip - 5 hours (Moderate)
Great hike for panoramic views of the Catskill Mountains and Hudson Valley, the trail follows a 7.3 mile in-and-back trail that takes approximately 5 hours to complete. Dogs are allowed off leash.
Windham High Peak & Burnt Knob Loop Trail - 6.75 mile trip - 6 hours (Moderate)
The Windham Path -Multi Use Trail on Rt 23 just East of Windham. Beautiful 1.5 mile loop featuring mountain views. streams, meadows, beaver dams and foot bridges. It is a multi use trail great for all levels of abilities, walking, running, biking and xc skiing.
Acra Point Loop Trail - 5.06 mile trip - 3.5 hours (Easy). Nice view of Blackhead Mountain Range and walk along Escarpment Trail.
Point Look out, Acra, NY. On a clear day, the panoramic view from this location encompasses the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York, and the Connecticut Valley.
Blackhead, Black Dome, Thomas Cole - 6.68 to 8.56 mile trip - 5-6 hours. 1,795 vertical climb. Difficult to Very Difficult hike. Great Views from Blackhead and Black Dome Mountains.
Camel's Hump and Thomas Cole Mtn - 6.12 mile trip - 3.5 hours (Moderate). Very nice in the Winter. Easy way to approach the Blackhead Mountains.
Blackhead Mountain to Arizona Mountain to Dutcher's Notch - 7.44 mile trip - 4.5 hours (Difficult). Outstanding views and nice walk across the ridge of Arizona Mountain. Rarely used trail.
Dutcher's Notch - Arizona Mountain - Blackhead Mountain - 9.50 mile trip - 6 hours (Difficult). Outstanding views from Dutcher's Notch to Blackhead along the Eastern Escarpment. Rarely used trail.
Dutcher's Notch and Arizona Mountain - 7.34 mile trip - 5 hours (Moderate). Outstanding views from Dutcher's Notch to Arizona Mountain along the Eastern Escarpment. Rarely used trail.
Round Top to Dutcher Notch to East Kill Falls - 7.20 mile trip - 5 hours (Moderate). Moderate walk up the old rocky Colgate Carriage Road to Dutcher's Notch.
Colgate Lake to Dutcher Notch - 9.24 mile trip - 5 hours (Easy). This is one of the few easy level walks in the woods. You will have a number of fields, apple orchards, conifer forest, five bogs, and bridges.