3.3
(2)
95
hikers
01:36
5.81km
100m
Hiking
The Leatherman's Cave Loop offers a captivating journey through varied terrain, where you'll discover the impressive Leatherman's Cave with its massive overhanging ledges and intricate rock formations. The trail winds through woodland sections and past Black Rock Pond, providing a scenic backdrop for this moderate 3.6-mile (5.8 km) hike. With…
Last updated: June 9, 2026
Waypoints
Start point
Parking
Get Directions
2.30 km
Highlight • Cave
Tip by
5.47 km
Highlight (Segment) • Trail
Tip by
5.81 km
End point
Parking
Way Types & Surfaces
Way Types
3.37 km
2.16 km
100 m
< 100 m
< 100 m
Surfaces
3.19 km
2.36 km
164 m
< 100 m
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Elevation
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Weather
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Today
Sunday 6 September
22°C
14°C
62 %
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Max wind speed: 14.0 km/h
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This route was planned by komoot.
This route is rated as moderate. While it's not overly long at just under 6 km, it does include some elevation changes, making it a good option for hikers looking for a bit of a challenge without being overly strenuous.
The trail features varied terrain typical of the Ward Pound Ridge Reservation, including woodland paths, some rocky sections, and gentle ascents and descents. You'll navigate through forests and open areas, offering a diverse hiking experience.
Yes, dogs are generally welcome in Ward Pound Ridge Reservation, including on this loop. However, they must be kept on a leash at all times to protect wildlife and ensure the safety of other visitors.
Ward Pound Ridge Reservation typically has a parking fee, especially during peak seasons or weekends. It's best to check the official Westchester County Parks website for the most current information on fees and operating hours before your visit.
Spring and fall are often considered the best times to hike this loop. In spring, you'll see new growth and wildflowers, while fall offers stunning foliage. Summer can be pleasant, but be prepared for heat and insects. Winter hiking is possible, but check conditions for ice or snow.
The main highlight of this route is The Leatherman's Cave, a fascinating natural rock shelter associated with the legendary 19th-century wanderer. You'll also pass through the Michigan Meadow Marsh Connector, offering scenic views of marshland. The trail itself winds through beautiful woodlands.
Yes, the route utilizes sections of several official trails within the park. You'll find yourself on parts of the Red Trail, Green Trail, Leatherman's Loop, and Yellow Trail, among others, as you complete the circuit.
The Leatherman's Cave Loop is located within Ward Pound Ridge Reservation. Parking is available at designated lots within the reservation. It's advisable to arrive early, especially on weekends, as parking can fill up quickly.
While rated moderate, the trail's length and elevation changes might be a bit much for absolute beginners. However, those with some hiking experience or a reasonable fitness level should find it enjoyable. If you're new to hiking, consider starting with shorter, flatter trails in the reservation first.
The cave is named after the 'Leatherman,' a mysterious 19th-century figure known for his distinctive leather clothing and his regular 365-mile circuit walk through Connecticut and New York. He reportedly used various rock shelters, including this one, as resting places during his decades-long journey.
Restrooms and water fountains are typically available near the main parking areas or visitor centers within Ward Pound Ridge Reservation. However, there are no facilities directly on the trail itself, so it's essential to carry enough water and plan accordingly.
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