There are four trailheads on the mountain: Ledges, Bald Peak, Southwest Ridge, and Firewarden’s. All trails connect and lead to the summit.
Ledges Trail (1.8 miles):
This blue-blazed trail, provides another access from Mountain Road to the primary summit of Pleasant Mountain offering scenic overlooks along the way. Elevation gain is 1,600 feet and the parking area is adjacent to fire lane 54.
ledges trail parking
Fire Warden’s Trail (2.3 miles):
This trail provides access to Pleasant Mountain's summit from the northwest via Wilton Warrent Road and is used by snowmobiles in the winter. Trail is blazed with red and has a 1,500 foot elevation gain.
fire warden's trail parking
Southwest Ridge Trail (2.7 miles):
This trail provides access to Pleasant Mountain's southwest and primary summits via the Denmark Road. The trail is blazed with yellow with rock cairns.
southwest ridge trail parking
Bald Peak Trail (2.4 miles):
This blue-blazed trail is accessed from Mountain Road and has a 1,900 foot elevation gain. The trail leads up to Big Bald Peak and then swings south to Pleasant Mountain's summit.
bald peak trail parking
Sue’s Way (0.5 miles):
This orange-blazed trail provides access from the Bald Peak Trail to the top of the Shawnee Peak Ski Area. There is a 500 foot elevation gain. Orange blazing. Access via Bald Peak Trail or North Ridge Trail.
North Ridge Trail (0.8 miles):
Blazed with white, this trail connects Sue's Way back with the Bald Peak Trail to create a loop. The elevation gain is 200 feet.