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Hiking trails & Routes
United States
New York
Westchester County

Leatherman's Cave Loop

Moderate

3.3

(2)

95

hikers

Leatherman's Cave Loop

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

A

Start point

Parking

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1

2.30 km

The Leatherman's Cave

Highlight • Cave

One of the area's most renowned landmarks is The Leatherman's Cave. It received its name from a man in the late 1800s who earned his nickname due to his distinctive …

Tip by

2

5.47 km

Michigan Meadow Marsh Connector

Highlight (Segment) • Trail

Following this connector path guides you through the captivating Michigan Meadow Marsh, surrounding you in a breathtaking environment. As autumn arrives and the leaves transform into shades of gold, the area transforms into a picturesque scene.

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B

5.81 km

End point

Parking

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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Weather

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Today

Sunday 6 September

22°C

14°C

62 %

Additional weather tips

Max wind speed: 14.0 km/h

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Frequently Asked Questions

What is the difficulty level of the Leatherman's Cave Loop?

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.

What kind of terrain can I expect on this trail?

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.

Are dogs allowed on the Leatherman's Cave Loop?

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.

What are the entrance fees or permits required for Ward Pound Ridge Reservation?

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.

What is the best time of year to hike the Leatherman's Cave Loop?

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.

What can I see along the route?

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.

Does the trail intersect with other paths in Ward Pound Ridge Reservation?

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.

Where is the trailhead and is there parking available?

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.

Is the Leatherman's Cave Loop suitable for beginners?

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.

What is the history behind the Leatherman's Cave?

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.

Are there any facilities like restrooms or water on the trail?

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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