February 5, 2009 – The Leatherman's Loop

How Do You Train?: Whippoorwill Park Trails

November 10, 2011February 5, 2009 by leathermansloop

Whippoorwill Park is in New Castle (Chappaqua), NY close to Greeley High School (see map here). It is 167 acres and has a perimeter loop of around 2.5 miles. There is also an unmarked “purple trail” that is one way, terminating at Whippoorwill Lake Rd. If you add the purple trail to your run your … Read more

The Loop

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 Lottery registration lottery signup will be held over 4 FULL DAYS from January 6 - January 9, 2023. Drawing for spots in the Loop will be on Friday January 13, 2023 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.

To keep up with Loop news,

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