The group we are affiliated with organizes a 5 mile trail race and kids trail race at Muscoot Farm in Katonah, NY called Run The Farm. Race dates are in May and October. Check details, photos, and recaps at the runthefarm.org website.
Another race that was developed by members of the Leatherman Harrier Sunday Runners group is the Raven Rocks Run, held the second Sunday in November (the Sunday after the NYC Marathon). The Raven Rocks Run is a 10k that starts and finishes in The Meadow at Ward Pound Ridge Reservation (the same place where the Leatherman’s Loop starts and finishes). Instead of the River and Mud, the Raven Rocks course seeks the hills and heights of the park. The Raven Rocks Run was inaugurated in November 2015 and will be returning again this coming November!
We also helped to start the Fire Tower Trail Half Marathon & 10k which is held in June. It is a tough, hilly race for both distances and each distance passes by the restored fire tower atop Cross River Mountain.
We also support many local trail races by participating in them, volunteering at them, and photographing them.

We have pulled many of the local Westchester/Fairfield trail races together to form the Trail Mix Trail Series. Started in 2014, this series has grown by the strength of the runners into seven races. See the Trail Mix website for information and current standings.
This is a comprehensive listing of Trail Races in the NY/NJ/PA/CT area for those interested in participating in or volunteering at more trail runs.
The list is compiled and published by friend-of-the-Loop and website contributor Chris Jaworski. Chris is a member of the Essex Running Club pictured here with members who ran the Leatherman’s Loop.
The listing Chris has compiled and maintains is a great resource for the question we get a lot about other trail races in the NYC metro area. If you know of a race not on this listing, let us know and we will pass it along to Chris.
Some trail races (and a few very select road races) we have personally run in the past or plan to run include:
- John Jay 5k Trail Race (Cross River, NY) Early April
- Mudders and Grunters (Yorktown NY) 5M (late March)
- Bimblers Bash (Guilford CT) 10k-ish (early April)
- Doug Wood 5k XC Trail and Fun Run (Northport, NY) (Mid April)
- Rock the Ridge 50k run and relay (New Paltz, NY) (early May)
- A Mild Sprain 4.25M (Yonkers NY) (Early June, on hiatus)
- Where the Pavement Ends 4.25M (Ridgefield CT) (mid September)
- Sarah Bishop Bushwhack 10k (North Salem, NY) (late September, on hiatus)
- Paine to Pain 13.1M (New Rochelle NY) (Early October or late September)
- Run the Farm 5M (Katonah/Somers, NY) (late October)
- Raven Rocks Run 10k (Cross River, NY) (second Sunday in November)
Other listings of trail races throughout the world (let us know any other listings you know of):

