hiking – The Leatherman's Loop

Walking (and Running) Wild Lewisboro

November 10, 2011January 16, 2009 by leathermansloop

The Lewisboro Land Trust has put together a fantastic booklet for trail lovers (runners, walkers, and hikers can all benefit) called “Walking Wild Lewisboro.” Walking Wild Lewisboro contains details about 20 preserves and parks in Lewisboro, including the Ward Pound Ridge Reservation (#20 in the map shown here) which has its entrance and about 1/3 … Read more

Loop starts at 9am.

Please see FAQ for arrival time advice.

The Leatherman's Loop is a 10k trail race held each spring. The event has been held annually at the Ward Pound Ridge Reservation in Cross River, NY since 1987 and we believe it is the largest trail race on the East Coast of the United States.

Loop Registration information is here.

Loop Lottery registration lottery signup will be held over 4 FULL DAYS from January 5 - January 8, 2024. Drawing for spots in the Loop will be on Friday January 12, 2024 will be announced via email on that day. If you need to check your lottery status, you can search for your name by clicking here.

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Check the tabs along the top of this page to find information about the Loop quickly.

Brief Video: Watch a brief video of the run to see what it's all about.

Loop History: Read about some Loop history from one of the Loop founders, Tony Godino.

Legend: Read about the Legend of the Leatherman.

Sunday November 12, 2023
Eighth Running!

We added the virtual Raven 100k Challenge in 2020 and by popular demand we are continuing to run the virtual challenge. Read about this month-long endurance challenge complete with badges and custom finisher woodallions!

Raven Rocks Run is the first new race at Ward Pound Reservation in nearly 20 years. The Raven Rocks 10k Run is a challenging course with great views, rocky climbs, ridgeline trails, hilly meadows, ravines, and the site of the former fire tower.

The race aims to help raise money to bring back and operate the fire tower at its former site so a whole new generation can enjoy the sweeping 360 degree views of Long Island Sound, Connecticut, the Hudson Highlands, and New York City it will afford.

Race was run the first time in 2015.

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