Events
Leatherman's Loop
Information
The Leatherman's Loop is put on by Leatherman's Loop Races.
Other races to check out: FALL Run the Farm (Oct 25, 2026) • Raven Rocks Run (Nov 8, 2026) • SPRING Run the Farm (May 23, 2027) • Fire Tower Trail Half Marathon & 10k (June 6, 2027)
The Leatherman's Loop is a 10k trail race held in the spring (April 25, 2027). Start time is 9am. (ARRIVE at the park BY 8AM if you are registered to run!)
If you have questions about the race, visit the Loop website or specifically the Loop FAQ page at the website.
You can follow us on Instagram: https://instagram.com/leathermansloop and Facebook: https://facebook.com/leathermansloop
Due to the popularity of the event, Loop entry is via Lottery. For more information, visit our Loop Lottery FAQ page here.
We are always grateful to our race volunteers! If you'd like to sign up to volunteer, visit this page: https://leathermansloop.org/volunteer
Please put leathermansloop@gmail.com and info@runsignup.com in your address book so our emails to you and the confirmation emails from RunSignUp.com do not get tagged as spam.
Thanks!
-Rob, Ciorsdan, and the Leatherman Harriers volunteers
PS: two additional notes:
1.) The registration cost of the Leatherman's Loop incorporates the park's entry fee into the registration cost -- so the park does not have to collect the parking fee separately from each entrant on race morning. Long ago we figured out it was more efficient for us to pay the park that fee directly rather than have hundreds of cars line up at the entrance fumbling for cash at the entrance gate to the Rez on race morning.
2.) Dogs are not permitted to run in the Loop. In 2020 the USATF began a new policy prohibiting dogs from running in races they sanction and insure. The Loop is a USATF sanctioned and insured race. Leashed dogs are welcome at the park anytime.
Contact Us
If you have any questions about this race, click the button below.
Location
Reservation Road
Cross River, NY 10518 US
View Location on Map
YES! Visit https://leathermansloop.org/frequently-asked-questions for a detailed FAQ listing we have put together over the past 20 years.
Some of the questions are below, but not all of them. See this link above for the best and most complete FAQ until we get it all moved over here (if possible!)
NO! — It has been over 20 years since we had same day registration for the Loop.
Same day, walk-in, last minute registrations are not allowed and have not been since 2007. We typically have hundreds of people waiting to get in who missed the lottery. It is simply not fair to the others who are registered and those who were shut out and ahead of you.
Unless you are a confirmed runner who has received a confirmation email and is listed on the confirmation page, please don’t come expecting to run in the race.
You can check our registration page here for the link to make sure you are on the registered runner list: https://leathermansloop.org/registration/ If you are not on the list linked to at this page — you are not registered! Please verify before coming to run on Loop morning.
Get in touch with us BEFORE LOOP MORNING if you think you are registered for the Loop but your name is not on the list at the link above.
On the day of the Loop you will be turned away if you are not registered. Our list is final.
No -- Runners CANNOT USE ANOTHER RUNNERS BIB
Anyone we see doing this will have their names changed to TURKEY in the results and be banned from future Loops.
People who do this play havoc with the results and are also cheating the rest of the running field by not supporting the race.
As an example: In a recent Loop, a 20 year old male ran using a 50 year old female’s bib number. The results for the “woman” put her (really him) as the top finisher in the F50-59 category. This pushed the real first place finisher in that division to second. Another example is the 18 year old who ran and won 3rd place in the F40 category, pushing out the rightful 3rd place winner from winning their pie. This is not good sportsmanship. We only discovered these problems after the awards were made. It may not seem like a big deal to you when you do it, but it is a big deal to us and the people who are wrongfully passed over. Just don’t do it please. Also, your name goes on a list of “runners not eligible to win the loop lottery” if you bandit the race.
Also, when you sign up to run the Loop, you sign a waiver. When you give someone else your number, they haven’t signed a waiver. Our insurance company doesn’t like that. If something happens to them, they’re not covered. When you register for the race, the waiver also states you will not give your bib to another runner.
If you can’t register for the Loop or miss out in the lottery, please consider volunteering (see below), coming to run during a course check in the weeks leading up to the loop, cheering your friends/family on, or registering for another local trail race. Plus there’s always next year!
PLEASE READ BELOW BEFORE COMING to the park WITH YOUR DOG.
We have been required by our insurance company to prohibit dogs running in the race.
This is a new policy starting after the 2019 Leatherman’s Loop. Please contact us if you have any questions.
Spectator Dog Rules:
- Dogs must be leashed at all times. (This is a county law for all parks.)
- No long leads or retractible leads allowed.
- You know your dog best, so make sure they can deal with large numbers of people at the park (and many other dogs). If they can’t deal with it and they become a nuisance or a danger, you will be asked to take your dog home.
Note: No dogs are allowed in picnic areas at the park! Park rules.
Yes – there is a water station at just under the halfway point. It is just before the mud flats. There is also water available at the start/finish area near the teepee.
The Lewisboro Volunteer Ambulance Corps will also be stationed near the showmobile/bib pickup area in case you need medical attention.
Ward Pound Ridge Reservation in Cross River & Pound Ridge, NY. Click here for map with park entrance location marked.
It is a unique 10K trail run held in Ward Pound Ridge Reservation starting in Cross River and heading through Pound Ridge and South Salem, NY. Check this video, this article from the Lewisboro Ledger, this article from the first Loop in 1987, plus a bunch of other news articles on this site. Lots of photos can be found here.
Many people have described it but you must experience it for yourself to know what the Loop is. Get an annotated pdf map here showing the course, check a brief video about the Loop, or you can download the WPRR trail map showing the newest trails such as the Rock Trail and the Dancing Rock short loop.
No headphones – we have asked this starting in 2014 and driven by safety reasons and runner feedback.
First reason: being a good trail running citizen! The course is very crowded, especially at the beginning. You will not be able to hear anyone coming up behind you and yelling “on your left” or “on your right.” When you get to the single track trails, the twists & turns, and the funneling of runners, this can be a safety issue.
Second: Your music player will very likely be wrecked by the various water and mud hazards on the course. A slip and fall at the wrong time will get your electronics an appointment with the rice baggie… (which doesn’t work so well with mud)
Third: you miss a vital part of the Leatherman’s Loop experience: the sounds of the race, the gleeful whoops of runners who have encountered the next obstacle, and the musical surprises on the trail waiting for the runners to pass by.
If you use music as a motivational spur for your solo workouts, consider this: you are NOT solo on this run… The 1,200+ other people around you should provide sufficient motivation and energy for your time on the trail during the Loop!
No. Registrations are non-refundable and non-transferable (that means no resale of bibs). We don’t do deferrals. See this article for some reasons why (excerpt below).
In essence, we hope you understand our simple approach meets our desire to do four simultaneous things: • Put on a top quality event; • Keep the registration fees modest; • Maximize the efforts of our volunteers toward race-related duties; and • Raise money to improve the trails and park.
Our all-volunteer organization does not have time for a rush of transfers and deferrals in the month or so before the loop. People still ask, and the answer is no. If you are reading this, thanks for not asking and we are very sorry we can’t accommodate you.
No, we do not offer deferrals of registrations from year to year. See above.
No. Registration is non refundable and non transferable. See above.
The Leatherman’s Loop was started by four trail running friends back in 1987. Check this first edition of the Founder’s Newsletter to read some background and history of the Loop. It is a great story and even better when Tony or one of the other founders tells it in person.
The current group guiding the Loop is here and is helped by an experienced volunteer group of 40-50 people each year to help pull off this fantastic event (plus “Run the Farm” in October and other Trail Mix Series events during the year).
Either: click here (to sign up for our email list) or here (to contact us via a web form where you can enter a question). We also have a facebook page, a twitter feed, and you can follow us on tumblr. One or more of those should do it, especially since email is very unreliable.
For the email list sign up you will get a confirmation immediately from our email company that you must click on to actually confirm you own that email address. This is an automated way of preventing random people from signing others up for a mailing list they don’t want to hear from.
For the “contact us” form, we usually get the message within a day or so (and sometimes sooner). It may take a bit to get back to you — or you might get a response the same day — but we should respond. If we don’t please send another message — we won’t mind!
The Loop starts at 9AM. We recommend arriving before 8:15 if you have done this before. Get here earlier than that if you are new to the Loop.
Remember, there are around 1,100-1,300 other people (runners, spectators, and volunteers, give or take a few) arriving around the same time through a single-lane road.
You will need time to park (possibly far away from the bib pickup), get yourself ready, pick up your bib (and shirt if ordered), put your shirt back in your car, check the course map, meet up with friends, and gather across the meadow to the starting line. If you have extra time, check out the level of the Cross River at the final water crossing near the start line.
There are port-o-sans in the picnic area adjacent to the Meadow parking lot (maps). There are also restrooms at the park entrance by the entry gate. Could be a timesaver — plus they are not port-o-sans!
Yes. You should make a booking well ahead of time through the park. The night before the loop is very popular! No surprise.
Check their website here: http://parks.westchestergov.com/ward-pound-ridge-reservation/ward-pound-ridge-fees for contact information. If you do camp out overnight you might think about bringing a bike to get down to the Meadow parking lot in the morning rather than driving your car due to the crowds.
No and No. Regular running shoes are fine for the Loop.
However, trail running shoes are a nice plus and will help with traction. But we have no boulders and only a few rock faces to navigate. Most of the (above water) trail is single track dirt/mud or slightly wider.
We have kept our (muddy) shoes from each loop. After a trip through the washer and dryer they are good to go. Some folks have retired their sneakers after a run on the Loop. The course is honored to have met those sneakers and helped them run their last race.
There is no upper boundary!
Or do you mean how old kids have to be? This is one decision you know your kids best — it is up to you to decide. One thing we do know is kids younger than 10 should NOT run the course solo.
The choice of running the Loop with your young child is up to you and you should stick with them the whole way.
Most kids who run are between 10-14 years old. The youngest to complete the course was 7 years old. One year a six year old started but turned around at the mud flats. After that we changed the minimum official registration age to 7 — but we are willing to accommodate special requests if you reach out with your request (leathermansloop@gmail.com).
Most kids attempt it for the first time after their parents have experienced it at least once.
There is a more thourough answer to this on the race website FAQ here: https://leathermansloop.org/frequently-asked-questions
Any other kid questions, contact us and we’ll do our best to answer your questions.
Early January the Loop Lottery opens. In 2012 and going forward, race entry became a full lottery.
Yes we have early bib (& shirt if ordered) pickup the day before the Loop at the Reservation.
It will be open from 9am - 12pm the day before. And then we will reopen at 7am on race day.
Parking fee is included with race registration.
Normally there is a $10 entry/parking fee but for efficiency we incorporate the fee into registration.
In the meadow just after the entry to the park.
The meadow parking lot usually fills up before 7:30am and the rest of the cars are parked on the grass of the upper meadow.
There is no formal gear check.
People usually leave valuables in their car.
Clothing items are sometimes left near the start line or finish area where they can be picked up after runners finish.
There are restrooms near the parking/bib pickup area.
There is one porta potty about 2 miles into the race in the Kimberly Bridge picnic area parking lot, but it is not reserved for runners and don't count on it being available as 1000 people run by.
In the meadow parking lot inside of the showmobile on race day. Just outside of the showmobile for early pickup the day before.
We have sweeps following behind the slowest runners. Don't make them late for lunch.
Shirts are available and are additional cost.
Prizes for overall and age group winners (1-2-3) are pies of varying sizes and flavors.
In the Meadow Lot at Ward Pound Ridge Reservation.
Loopy
AIYou are about to initiate a chat with an AI assistant (not a person).
By clicking “Agree and start chatting”, you agree to the collection, recording, storage and processing of this chat communication as outlined in our Privacy Policy.