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Hiking trails & Routes
United States
New York
Westchester County

Leatherman's Loop Trail

Moderate

4.7

(9813)

11,640

hikers

Leatherman's Loop Trail

02:29

8.82km

180m

Hiking

The Leatherman's Loop Trail offers a truly engaging experience through the diverse landscapes of Ward Pound Ridge Reservation. You'll find yourself on narrow singletrack, wider forest paths, and old woods roads, navigating natural obstacles like roots, rocks, and historic stone walls. The trail winds through beautiful pine forests, particularly at…

Last updated: June 9, 2026

Waypoints

A

Start point

Parking

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1

3.90 km

View of Cross River Reservoir

Highlight (Segment) • Viewpoint

This trail offers a pleasant, shaded route, revealing breathtaking views of the Cross River Reservoir. Along the way, you'll encounter several rock walls and bridges, adding to the adventurous atmosphere. …

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2

6.52 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 …

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B

8.82 km

End point

Parking

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Way Types & Surfaces

Way Types

4.06 km

3.35 km

1.21 km

127 m

< 100 m

Surfaces

5.27 km

3.29 km

169 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.

Highest point (190 m)

Lowest point (110 m)

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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

Where is the trailhead for Leatherman's Loop Trail and what are the parking options?

The Leatherman's Loop Trail is located within Ward Pound Ridge Reservation in Cross River, New York. Specific trailhead parking information for the Loop itself is typically found within the reservation. Ward Pound Ridge Reservation has multiple parking areas; it's advisable to check the park's official website for the most current parking details and any potential fees.

Are there any entrance fees or permits required to hike in Ward Pound Ridge Reservation?

Yes, Ward Pound Ridge Reservation, where the Leatherman's Loop Trail is located, typically charges an entrance fee per vehicle. These fees can vary by season and day of the week. It's best to check the official Westchester County Parks website for the most up-to-date information on fees and operating hours before your visit.

What is the terrain like on the Leatherman's Loop Trail?

The trail offers a diverse and challenging experience with a mix of singletrack and wider doubletrack sections. You'll encounter natural obstacles like large logs, stone walls, and significant mud flats that can be quite deep. Defining features include at least two river crossings and a steep, 45-degree sand hill known as "The Wall" in a former quarry. The route also includes steady climbs and descents, winding through bright pine forests and past rock formations.

How long does it typically take to hike the Leatherman's Loop Trail?

Based on komoot's data, the Leatherman's Loop Trail typically takes around 2 hours and 28 minutes to complete. However, this can vary significantly depending on your pace, the trail conditions (especially mud and river levels), and how much time you spend enjoying the scenery and unique obstacles.

Is the Leatherman's Loop Trail dog-friendly?

Yes, the Leatherman's Loop Trail is generally dog-friendly, as it's located within Ward Pound Ridge Reservation. However, dogs are typically required to be on a leash at all times. Given the challenging terrain, including deep mud and river crossings, ensure your dog is comfortable with such conditions and that you bring appropriate gear for them.

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

Spring and fall are often considered the best times to hike the Leatherman's Loop Trail for pleasant temperatures and vibrant scenery. However, be aware that spring can bring significant mud washouts and higher water levels in the river crossings. Summer can be hot and humid, while winter offers a different, often quieter, experience, but with potential for ice and snow. Always check current trail conditions before heading out.

What unique landmarks or viewpoints can I see along the route?

The trail offers several notable features. You'll find a scenic View of Cross River Reservoir, providing expansive water views. Another significant landmark is The Leatherman's Cave, which has historical ties to the legendary "Old Leatherman." The trail also features "The Wall," a steep sand hill in a former quarry, and various rock formations.

What should I wear or bring when hiking the Leatherman's Loop Trail?

Given the varied and often challenging terrain, sturdy, waterproof hiking boots are highly recommended, especially for the river crossings and extensive mud flats. You might even consider bringing a spare pair of socks or shoes for after your hike. Trekking poles can be helpful for stability on steep sections and river crossings. Always carry enough water, snacks, and navigation tools. Dressing in layers is also wise due to potential weather changes.

Is the Leatherman's Loop Trail suitable for beginners?

The Leatherman's Loop Trail is generally considered moderate to strenuous for hiking, largely due to its varied and challenging terrain. The river crossings, deep mud flats, and the steep ascent of "The Wall" require good footing and can be physically demanding. While not impossible for beginners with good fitness, it's not a typical easy stroll and might be a significant challenge for those new to hiking.

Does the trail intersect other well-known paths?

Yes, the Leatherman's Loop Trail is part of a larger network within Ward Pound Ridge Reservation. This route specifically covers sections of the Leatherman's Loop, Green Trail, and Red Trail. You may also encounter portions of the Yellow Trail, Covered Bridge, Richard's Preserve trail, and various connector trails like the Leatherman Overlook Trail and Armstrong Loop.

What makes the Leatherman's Loop Trail so notable?

The Leatherman's Loop Trail is most famous for being the course of a unique 10k trail race, one of the oldest and largest in New York State. Its notoriety stems from its "steeplechase-like" obstacles, which include significant river crossings, challenging mud flats, a quarry climb known as "The Wall," and diverse singletrack sections. The trail's historical connection to "The Old Leatherman," a legendary wanderer, also adds to its intrigue, offering an adventure that goes beyond a typical walk.

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