Starter Series: Leatherman's Cave

Union Square
Union Square
Broadway at East 18th Street
to 6:00PM
8:30AM to 6:00PM
Arrive by 8:15AM
6.4 miles
600 feet
elevation gain

This trip is currently unavailable.
About the trip

Beautiful Trail in Ward Pound Reservation

What We Love

  • Scenic rock formations
  • Beautiful flora
  • Hear history and stories from your guides
  • Peaceful, quiet park

Your Day

Retrace some of the steps of the legendary Leatherman, a mysterious figure from the 19th century who spent his days traveling between the Connecticut and Hudson rivers in his homemade leather suit and his nights seeking shelter in caves. Our hike will take us through Ward Pound Ridge Reservation in Westchester county, where we’ll travel a scenic six miles, taking in views from atop the ridge and hiking past formations like Raven, Castle, and Spy Rocks. We’ll finish the hike with a visit to the Leatherman’s Cave, a spot where our wandering figure often rode out the harsh winters.

Perfect for : First time hikers, experienced hikers looking for a relaxing day

Photo Credit: Mountain Project

Share Trip
Level 4/10
600 feet elevation gain
6.4 miles
Union SquareBroadway at East 18th Street
8:30AM to 6:00PMArrive by 8:15AM

Here’s what you need


Essential Gear
  • Lunch
  • Ample snacks
  • At least three liters of water
  • Backpack. Need a recommendation? Check out Deuter!
  • Weather-appropriate clothing. For a great selection and discounts, visit our partners
  • Sunscreen
Recommended Gear
  • Hiking poles
  • Gaiters


Essential Clothing
  • Comfortable athletic clothing
  • Hiking boots with non-cotton socks
  • Hat
  • Jacket
  • Dress in layers to adapt to changing temperatures

What's Included

  • Expert guides
  • Transportation
  • Park permits
Not Included
  • Meals
  • Gratuity for your guide

Drive to Meet

Have your own transportation? Select the "drive to meet" option at check out. You'll meet your guide at the Michigan Road Parking Area in Ward Pound Ridge Reservation at 9:45 AM.


Weather conditions can be quite different from the city in the mountainous regions we visit. Temperatures can be quite cooler as we head north or to higher elevations. Keep your eyes out for an email from our team a few days in advance of your trip. That email will provide updated weather conditions and will alert you to anything additional you should put in your pack to prepare. We head outside in any weather, as long as we know it's safe, and we don't let a little rain or wind ruin a chance for an adventure. You can contact us at [email protected] if you have any questions about preparing for trail conditions.


Level 4

Ideal for Active Beginners and Moderate Hikers

Level 4 trips balance physical and aesthetic components of the day. Get your heart pumping on intermediate terrain with some rock scrambles and multiple peaks, then enjoy a well-earned break with a stunning view. These trips are effective preparation for even more challenging weekend-long trips.


Trail time ranges from for four to six hours. You should be in good physical shape and exercise at least three times a week to get the most out of the day.


You’ll be traveling five to eight miles on this trip, the average distance run in an hour-long soccer game.


You’ll be hiking on steadily rising terrain with loose rock surfaces, switchbacks, roots and small boulders.

Elevation Change

Up to 1,500 feet per day.


Up to 6,000 feet.

You may also like…

Winter Hike & Howl

November 23, 2019
Level 3/10
Union Square

Lake Awosting Hike

November 23, 2019
Level 4/10
Union Square

Winter Hike & Whiskey Tasting

November 24, 2019
Level 3/10
The North Face

3500 Series: Indian Head Mountain

November 24, 2019
Level 7/10
Upper West Side
View More Trips