Ward Pound Ridge Southwest Loop to Leatherman's Cave


This loop hike traverses the hills of this Westchester County park, climbing to a panoramic lookout over the Cross River Reservoir and the interesting Leatherman’s Cave, and passing a number of other features of interest.

4.5 hours
6.5 miles
Route Type:
Allowed on leash
First Published:

Daniel Chazin


Leatherman's Cave. Photo by Daniel Chazin.


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Trail Conference volunteers maintain trails in this park.
Trailhead GPS Coordinates
Driving Directions

Take I-684 exit 6 (Route 35). Turn east and go 3.7 miles to N.Y. Route 121. Turn right onto Route 121, cross a bridge over the Cross River, then immediately turn left and enter Ward Pound Ridge Reservation. Continue for 0.7 mile to the tollbooth (an $8 parking fee is charged on weekends, daily in the summer). Make the first right beyond the tollbooth onto Michigan Road, and continue for 0.7 mile to a parking area just before a turnaround circle at the end of the road (if this parking area is full, additional parking is available uphill to the left).


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 brown 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 copy of the 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, you’ll pass a kiosk on the right (trail maps are available here) and come to a fork at intersection #70. Bear right, following the red and green arrows, then bear right again at the next intersection (#53), as one leg of the Green Trail leaves to the left.

Proceed ahead on the Red and Green Trails, passing intersection #54 on the right. At intersection #31, turn right onto the Leatherman’s Loop Trail (marked by “LL”-on-white blazes). When you reach the next intersection (#26), proceed straight ahead, but turn left at the following T-intersection (#27) and continue to 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 this 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 interesting overhanging rock, you’ll reach intersection #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 in! After exploring this interesting feature, retrace your steps to intersection #29 and turn left (east), now following the “LL” blazes along a wide woods road.

When you reach intersection #28, the Leatherman’s Loop Trail turns left, but you should bear 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 intersection #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 intersection #32, you’ll parallel a stream on the left and climb gradually on a winding woods road. When you reach intersection #34, bear right to continue on the Red and Green Trails.

After descending a little and passing a wetland on the left, you’ll reach intersection #38. Here, the Red and Green Trails turn left, but you should turn right onto a white-blazed trail. At the next fork, the trail bears left and crosses under a power line to reach intersection #39. Turn left onto the Rocks Trail (marked with “RT”-on-white blazes) and climb to the Bear Rock Petroglyph (on the left side of the trail), which features a carving by Native Americans 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 intersection #60. Turn right at this junction and follow a white-blazed trail up to Dancing Rock – a flat rock where farmers used to dance 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 (intersection #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 intersection #36. Turn right here, leaving the Rocks Trail, and continue along the Red Trail, which heads southeast, following a wide woods road through a valley. At intersection #47, a white-blazed trail begins on the right, but you should 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 intersection #48, turn sharply right onto the Rocks Trail and follow it for about 500 feet to Raven Rocks – a spectacular 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 intersection #48 and turn right onto the Red Trail.

At the base of a descent, you’ll come to intersection #21. Turn right, leaving the Red Trail, and follow a white-blazed trail, passing jagged, moss-covered cliffs on the left. After crossing a stream, you’ll reach intersection #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 intersection #19, where the Rocks Trail ends at a junction with the 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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