Leatherman's Loop 1993 shirt design - The Loop is the third largest trail race in the US as of 2013.

The Leatherman’s Loop is is a unique 10k trail run at Ward Pound Ridge Reservation in Cross River, NY. It features river crossings, mud flats, a quarry climb, beautiful pine forests, swamp land, and the Legend of the Leatherman.

The Leatherman’s Loop was founded in 1987 and has been run every year since then (except during the COVID restricted years of 2020 and 2021).

We believe it is the largest trail race east of the Mississippi River in the United States and possibly the third largest trail race* in the United States (depending on the year), with over 1,300 finishers in its 32nd and 33rd years 2018 and 2019. Runners consistently say it is one of the best trail races out there.

Registration information can be found by clicking here.

The Leatherman’s Loop is usually held the Sunday following the Boston Marathon in April each spring at the Ward Pound Ridge Reservation in Cross River/Pound Ridge/South Salem, NY.

It is the oldest trail race in Westchester County, NY and one of the oldest trail races in New York.

Check the Frequently Asked Questions (FAQ) listing for answers to common questions about the Loop. If you have 5 minutes, view a brief video of the loop taken by a runner while running the 2005 Leatherman’s Loop. You can also check our Loop History page.

If you want to get in touch, please contact us via our email address leathermansloop@gmail.com. If you would like to register for email updates, please sign up with our mailing list.


Tony, Judy, Rob, Mike and the Leatherman Harriers

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*Some of the biggest trail races in the United States we have heard about or run in include these below:

  • Living History Farms Race 7m (Urbandale, IA) – 7,500 runner limit. This is a cross country race through farm fields and stream crossings. Over 5,500 finishers recorded in 2013. This is by far the biggest trail race in the USA. Nothing even comes close. You could argue is it a “trail race” vs. a “cross country race” but the inclusion of so many trail features like water crossings makes it more of a trail race.
  • The Dipsea 7.5m (Mill Valley, CA) – 1,500 runner limit which it always comes close to (Oldest Trail Race in the US, runners are released in age and gender handicapped 1 minute intervals).
  • The Leatherman’s Loop 10k (Cross River, NY) –  1,325 runners finished in 2016.
  • Spillway Classic (Norco, LA) – varies each year. Top attendance was around 1,700 runners in 2010 but more recently the numbers have dropped to around 1,000 runners.
  • Hyner View Trail Challenge 25k  (Hyner, PA) – 960 runners finished in 2013 25k race, plus another 108 in the 50k! Numbers for this race keep increasing.
  • Ugly Mudder (Reading, PA)  7m – 784 finishers in February 2012, fewer in 2013.
  • Paine to Pain (New Rochelle, NY) – Nearly 700 finishers October 2012, growing with staggered start groups.
  • Mt Penn Mudfest 15k (Reading, PA) – formerly 800 runner limit. Course and location changes drove down capacity recently and new limit is 500 runners.
  • Mudders and Grunters 5m – (Yorktown Heights, NY) – 400-500 runners in its peak year, current year totals depends on how wintry it is at the end of March or early April.
  • Leadville 100 Mile – 952 started in 2013, 497 finishers. DNF folks all survived.
  • So many others … If you know of a larger trail race than one listed above from anywhere in the USA, please let us know. We are happy to update this very limited list and link to that trail race (let us know via this link).

Note we only include single (or staggered start) races in this list with a single distance and single finish. All day events like Tough Mudder, Spartan Race, etc. which have multiple different start times throughout a day or weekend are not included. We love those races — they are some of the biggest out there. While they share similar DNA — they are a whole different species than a typical trail race. If an event has more than one distance, we don’t combine the different events to get a total – we view them as different races.

We hope you can join us for the Leatherman’s Loop soon! Sign up for our email list here.

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