Hike Leatherman's Loop



1.25 miles

Elevation Gain

1183 ft

Route Type


Added by Jessica Cho

Leatherman's Loop is an approximately 1.25 mile loop hike located in Pound Ridge, NY, features rock formations, wooded area, a cave, and scenic overlooks.

This loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore.

The Ward Pound Ridge property is rather impressive. Parking in the lot is easy, but might get filled on nicer days and weekends. There is a map at the trailhead displaying the routes of various hikes. I would recommend snapping a photo of this map or taking a free one to-go, even though the trails themselves are relatively well-marked, since the park is quite large and complex.

The LL loop is a fun hike that will get your blood pumping. There are various inclines which can be a bit challenging, but the views at the top overlook are beautiful. While on this hike, stay alert and be sure to stray from the trail for a moment to check out Leatherman’s Cave before hiking to the top. It’s a fun feature to walk through and take pictures in.

Overall, this loop is great because it features all that you could want on a hike-- some rugged terrain, incline, and great views. There are also opportunities to extend the hike by getting on one of the other connecting trails to make for a longer adventure!

Note that there is a daily parking fee from May through Mid-October. But, this fee only applies on weekends from Mid-October to mid-May. This reservation is definitely kid and family friendly. Your whole crew can enjoy a day outside on the trails!

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Know for

Dog Friendly
Easy Parking
Family Friendly



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Always practice Leave No Trace ethics on your adventures and follow local regulations. Please explore responsibly!

We want to acknowledge and thank the past, present, and future generations of all Native Nations and Indigenous Peoples whose ancestral lands we travel, explore, and play on.

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