Peeskawso Peak Loop

This short but rewarding route begins and ends at the Monument Mountain parking lot off Route 7 near Great Barrington. Hikers typically ascend via the Hickey Trail, which climbs steeply through forest before reaching a junction near the ridge. Turn left onto the Peeskawso Peak Trail, where a short scramble leads to a narrow ridgeline with wide views of the Housatonic Valley, the Berkshires, and distant peaks in the Taconic and Catskill ranges. A signed spur trail leads to the Devil’s Pulpit, a dramatic rock pillar above the valley. From the summit area, continue along the Peeskawso Trail and descend on the Mohican Monument Trail, which winds gently downhill through wooded terrain and reconnects with the parking area. Dry conditions are best for this route, as the steeper sections and exposed ridge can become slick when wet or icy. The hike is popular and easily accessible, making it a great option for a scenic half-day in the Berkshires.