A relaxing hike through massive rock formations.
WHAT WE LOVE
- Relaxing pace
- Scenic rock formations
- Beautiful flora
- Hear history and stories from your guides
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.
Perfect for: First time hikers, experiened hikers looking for a relaxing day
Photo Credit: Mountain Project
- Your lunch
- Ample snacks
- At least two liters of water
- A backpack. Need a recommendation? Check out Deuter!
- Weather-appropriate clothing. For a great selection and discounts, check out our partners.
- Comfortable athletic clothing
- Hiking boots
- Expert guides
- Park permits
EASY ACTIVE - PERFECT FOR ACTIVE FIRST TIMERS
Level 3 trips will give you a broad sense of what hiking is all about. Test yourself on intermediate terrain, including light rock scrambles and ascending multiple peaks. The trips will invigorate you and inspire you to continue strengthening your hiking skills.
Three to five hours is standard. Prepare for the trip by jogging three miles or exercising two or three days a week.
Plan on getting starter miles under your belt. You’ll be hiking three to six miles on this trip, the average distance run in an hour-long basketball game.
You’ll be hiking on rolling terrain with bare rock surfaces, steeps, roots and small boulders.
There could be up to 1,000 feet of change in the day.
From sea level to 3,000 feet.
Drive to Meet Option
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 10:00 AM. See below for map.
This is my first trip. What should I expect?
Your guide will meet you at the departure location in a Discover Outdoors shirt and will be driving a passenger transport van. After introductions, you'll drive to your hiking location. The drive can be anywhere from one or one and a half hours (for most trips) to two and a half hours (for trips to the Catskills). Your guide will have lots of helpful information and lead you along the trail. You can expect some great views, interesting facts about the area, and lots of great conversations with your fellow hikers. After your trip is complete, you'll be dropped off at the same location as your departure.
What if I'm running late to the pick up?
We know how tough it can be to get around this city sometimes, but our trips depart on time. As a courtesy to your other adventurers and guides, please arrive at least 15 minutes early to your pick-up location so we can depart at our scheduled time. You're more than welcome to bring coffee and breakfast along to enjoy on the road. If you are running late, please contact your guide (whose phone number you'll receive via e-mail the week of your trip). Unfortunately we do not offer any trip credit for a missed departure due to late arrival.
What should I wear and bring?
All the information on what to wear and bring can be found on the trip's site in the pack tab. We recommend comfortable, athletic clothing in all seasons and advise against wearing cotton. Dressing in layers will allow you to adapt to changing temperatures. Hiking boots with wool socks are highly recommended, though sturdy sneakers are acceptable in warm and dry weather. In the winter and at times when we will be encountering snow or mud, hiking boots are required. You can contact us (212-579-4568 or firstname.lastname@example.org) for more information on trip conditions.
You should pack plenty of water (2-3 liters) and snacks, as well as a hearty lunch. It's also a good idea to bring an extra layer, a camera, a hat, and sunscreen in your pack. Oh, and don't forget to bring your sense of adventure!
How hard is this hike?
All of our hikes are rated on a scale of 1-10. You can find any trip's intensity on its main page, with a detailed description in the "intensity level" tab. We recommend that you review this information so you can be prepared for your day. If you have any doubts, please call or e-mail our office and we can provide more information on any trip's difficulty.
How many people will be there?
Our groups for hikes usually range from 8-14 people. Your group will have either one or two DO guides, depending on the trip.
Will I be the only solo traveler?
No way! Many individuals sign up to join our trips solo. The best part of a DO trip is meeting new people and being part of a group. Even if you show up as a party of one, you'll be leaving with lots of new friends.
What if I'm the slowest one?
We hike as a group, but sometimes people move at different paces - and that's completely ok! Our guides will always have your safety in mind and be keeping attentive track of the group. On longer or more difficult hikes, we'll have a sweep guide as well. As long as your group is keeping on schedule, there's no pressure to move fast; enjoy the trip!
Will there be bathrooms?
Once we get to our trailhead, nature is your bathroom! Your guide will brief you on leave-no-trace guidelines for using the bathroom responsibly. Always tell someone when you're stepping off trail to go.
What if I don't feel well?
Our guides receive medical training and are all certified Wilderness First Responders, so you're in good hands, but communicating is key. Please notify your guide if you don't feel well, are worried about a blister, or any other concerns. Also notify them in advance if you have any medical conditions or allergies.
What if there's rain in the forecast?
Forecasts change often in the mountainous areas we visit, so we keep a close eye on multiple weather forecasts leading up to a trip. We don't let a little rain or wind ruin a chance for an adventure. In most cases, the trees will provide quite a bit of cover from passing rain and, as long as you are dressed appropriately, you'll still have a great day. Please note that your guide may alter your trip itinerary in the case of inclement weather. If we decide that the weather is unsafe, we'll notify you by the afternoon before a trip via e-mail. Please note that there is no credit or refund due to weather unless the cancellation is made by DO, in which case we'll happily transfer your credit to a future trip.
How much should I tip our guide?
If you have a great day, a tip is a great way to thank your guide for their work. On our trips, a tip of 10-20% is customary.
Every journey starts with a first step. Whether you're new to hiking or just looking for a leisurely day on the trail, Starter Series trips will allow you to travel at a comfortable pace, over moderate distances, with plenty of time to enjoy the views. You'll get your heart pumping with some uphill and downhill stretches, but won't encounter any technical sections. There will be plenty of time to learn all about navigating trails, reading blazes, and how to practice leave no trace principles along the way.