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
6.0 miles
600 feet
elevation gain

Book Early & Save Price goes up $10 after Jan 30.
About the trip

Beautiful Trail in Ward Pound Reservation

What We Love

  • Relaxing pace
  • Scenic rock formations
  • Observe wildlife
  • Hear history and stories from your guides

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 relaxing yet scenic five 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.  This hike is ideal for those looking to spend a full day on the trail at a casual pace.

Depending on trail conditions, snowshoes or microspikes may be required. If so, they will be provided by your guide.

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

Photo Credit: Courtney Bassett

Your Guide
Arturo Quinones
Lead Guide

View Bio
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Level 4/10
600 feet elevation gain
6.0 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
  • Camera


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

Trip Package

  • 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.


Intensity Level

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.


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.

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