Ward Pound Ridge, Leatherman’s Cave Loop

Hike Description:
Ward Pound Ridge Reservation, the largest park in Westchester County, was opened in 1938. Over thirty farms were acquired for the park, and old stone walls, which once marked the boundaries between the various farms, criss-cross the reservation. The trails – most of which are woods roads – are open to hikers and equestrians, but bicycles are not permitted. Most trail intersections are marked by numbered signs posted on trees. These numbers are shown on the park map and referred to in the description below. Since the trail system in the park is complex, hikers should obtain a free park map before beginning the hike. This hike will generally follow the Red Trail, but with several detours to include a number of interesting features.

From the circle at the end of the road, bear right and follow a road blocked by a wooden gate. Just beyond, pass a kiosk on the right (trail maps are available here) and come to a fork at junction 70. Bear right, following the red and green arrows, then bear right again at the next junction 53, as one leg of the Green Trail leaves to the left.

Proceed ahead on the Red and Green Trails, passingjunction 54 to the right. At junction 31, turn right onto the Leatherman’s Loop Trail (LL-on-white blazes). At junction 26, proceed straight ahead, but turn left at the following T-intersection (junction 27) and follow the “LL” blazes, which proceed along a winding route to the top of a hill. Here, just to the right of the trail, rock ledges afford a panoramic west-facing view over the Cross River Reservoir. A wooden bench has been placed here and it is a good point to rest and take a short break.

Continue ahead along the Leatherman’s Loop Trail, which descends rather steeply on a footpath. After passing under an overhanging rock, you reach junction 29. Turn around, and you’ll see a small sign on a tree for the “Leatherman’s Cave.” Bear left and follow the white blazes uphill to the cave, which was one of the regular campsites of the “Leather Man,” who wandered along a circular 365-mile route in the 1880s, staying in each of 34 campsites or shelters along the way. The cave provides shelter from the elements but must have been rather uncomfortable to sleep there After exploring the cave, retrace your steps to junction 29 and turn left (east), now following the “LL” blazes along a wide woods road.

When you reach junction 28, the Leatherman’s Loop Trail turns left, but you turn right and continue on a white-blazed trail. After crossing a bridge across a stream, the trail begins a gentle climb. At the top of the rise, the white-blazed trail turns left at a fork and almost immediately reaches junction 30, where it ends at a junction with the Red and Green Trails. Bear right at the fork, now following red and green blazes. After continuing past junction 32, the trail parallels a stream on the left and climbs gradually on a winding woods road. When you reach junction 34, turn right to continue on the Red and Green trails.

After descending a little and passing a wetland on the left, you’ll reach junction 38. Here, the Red and Green Trails turn left, but you turn right onto a white-blazed trail. At the next fork, the trail bears left and crosses under a power line to reach junction 39. Turn left onto the Rocks Trail (marked with “RT”on a white tag) and climb to the Bear Rock Petroglyph (on the left side of the trail), which features a carving in the shape of a bear.Bear Rock Petroglyph. Photo by Daniel Chazin.

Continue along the Rocks Trail, which crosses under the power line once more and descends to reach junction 60. Turn right at this junction and follow a white-blazed trail up to Dancing Rock – a flat rock where farmers danced to celebrate the completion of the harvest – then continue along the white-blazed trail, which loops around and descends to end at another junction with the Rocks Trail at junction 37.

Turn right onto the Rocks Trail, which passes a small pond on the left and descends steadily to the next (unnumbered) junction, where the Red Trail joins from the left. Just ahead, you’ll come to junction 36. Turn right here, leave the Rocks Trail, and continue along the Red Trail, which heads southeast, following a wide woods road through a valley. At junction 47, pass a white-blazed trail to the the right. You bear left to continue along the Red Trail. After climbing a little, the trail bears left around a curve, with seasonal views to the right through the trees across the Stone Hill River valley.

When you reach junction 48, turn sharply right onto the Rocks Trail and follow it for about 500 feet to Raven Rocks – an unobstructed overlook over the Stone Hill River valley from a cliff (use caution, as there is a sharp drop here!) After taking in the view, retrace your steps to junction 48 and turn right onto the Red Trail.

At the base of a descent is junction 21. Turn right, leaving the Red Trail and follow a white-blazed trail, passing jagged, moss-covered cliffs to the left. After crossing a stream, you’ll reach junction 18. Here, the white-blazed trail ends, and you should turn left onto the Rocks Trail, almost immediately passing the Indian Rock Shelter on the right. Native Americans frequented this spot because the overhanging rocks offered protection from the rain.

Continue ahead on the Rocks Trail, which crosses two streams on wooden bridges. After crossing the second bridge, bear left, uphill, to reach junction 19, where the Rocks Trail turns left but you continue on with Red and Yellow Trails. Turn right, soon passing dramatic cliffs to the left. Continue to follow the Red and Yellow Trails along a wide woods road for about a mile, returning to the parking area where the hike began.

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