Leatherman’s Loop Trail Run Lottery to Open January 10th, 2014

Leatherman's Loop 10k trail run

Leatherman’s Loop News: Volume 28, Issue 1

The 28th Leatherman’s Loop trail run will be on Sunday, April 27, 2014 at Ward Pound Ridge Reservation in Cross River, NY.

All runners will sign up via

(Opens January 10th, 2014 at 12:00am)
Loop Lottery FAQ.
The Loop Lottery will open at 12:00am Friday, January 10th, 2014 and close Monday, January 13, 2014 at midnight — 4 full days total.

We encourage you to sign up as early as possible so you don’t forget. Once it is closed we won’t accept any new lottery entrants.

To sign up, visit the Leatherman’s Loop website during the lottery registration period and there will be links to the registration site.

Runners can enter the trail run lottery as part of a group. Each person from the group must register (or have someone register them) in the lottery. Runners can add their group name during lottery registration.

We have put together a list of frequently asked questions about the Loop Lottery. It addresses questions about group lottery entryduplicate registrations, t-shirt purchasing, trail run basics, and other questions you might have.

After the Loop Lottery entry closes on Monday, January 13th we will have the drawing for winners on or just after Friday, January 17th. Lottery winners and losers will be notified via email.

If you do not hear from us via email on January 17th or just afterwards, please contact us at leathermansloop@gmail.com so we can follow up.

We are interested in making the lottery as simple and hassle-free as possible. We appreciate any feedback or thoughts you have and can share with us. If you have any questions not covered above or in the Loop FAQ or the Loop Lottery FAQ, please get in touch via our contact form, or via our email address leathermansloop@gmail.com.

Thanks! See you on the trails…

-Tony, Mike, Rob, and the Leatherman Harriers

PS: If you are interested in running on the trails with a group of enthusiastic trail runners of all abilities, check out our club site at sundayruns.org and come out one Sunday morning and join in a group run. We run the trails all year round and always welcome new runners! We even do course checks of the Leatherman’s Loop to help you familiarize yourself with the terrain in the weeks before the event.

Leatherman's Loop 10k Trail Run

Loop 2014 Information


[UPDATE: Lottery selections have been made, registration is closed for 2014. If you are looking for 2014 Loop information, please visit the home page for the most recent updates. Advice on preparing for the Loop is here. You can check your registration status by searching here.]

The 28th annual Leatherman’s Loop is scheduled for April 27th, 2014 at 9am at the Ward Pound Ridge Reservation in Cross River, NY. Registration will be via Loop Lottery. We will let everyone know details on the Lottery in late 2013 or early 2014. (updated information here)

Once we know for sure that this is the date we will let everyone know. The race is contingent on county approval of the date and location as always.

Anyone who interested in training for the Loop should check the SundayRuns.org website and try to go on a few trail runs and course checks of the Loop. The Sunday Runs group meets every sunday at 8am to run on trails in the northern Westchester area.

Closer to the Loop we run course checks of the Loop course.

As a bonus the last few years we have run the course as a group on Super Bowl Sunday and christened it the “Looper Bowl” with optional river crossings. Between the mud, snow, freezing water, and ice it can make for an adventurous morning of trail running! Shorts and t-shirt recommended! Bring on the Winter!

Ward Pound Ridge Reservation History Book

There is a new book on the Ward Pound Ridge Reservation written by Beth Herr, former curator of the Trailside Museum, and Maureen Koehl, Lewisboro Town Historian. If you are interested in learning more about “The Rez” and the Trailside Museum this book is a great place to start.

The book is published by Arcadia Publishing. Arcadia has over 8,500 publications and specializes in high quality histories of small towns and historic sites.

The scope of the book covers the first 50 years of the park from 1925-1975.

From the book description on the Arcadia website:

9780738599052Ward Pound Ridge Reservation’s expansive landscapes and long-abandoned cellar holes tell a unique story. Its 4,315 acres, set aside by the Westchester County Parks Commission in 1925, hold within its boundaries a legacy left by the Native Americans and 18th- and 19th-century families who farmed the rolling fields and rocky hillsides. Marks of the 20th century include the remains of the Civilian Conservation Corps (CCC) encampment and the stone walls, trailside shelters, and roads built by these young men. Thousands of trees planted by the CCC stand tall, shading the reservation’s hiking and riding trails. Sitting amidst the park’s streams, cliffs, and hills is the Trailside Nature Museum, which was enhanced by the efforts of local garden club women. Indian rock shelters and a cave used by the Leather Man lend an air of mystery to the beauty and wonders of the park’s protected flora and fauna. Almost a century after its quiet beginnings, the reservation still invites visitors to enjoy and learn about the wonders of nature.

Leatherman’s Loop Founder’s Newsletter – Volume 4


Leatherman’s Loop founders note

Twenty seven years ago Dave Cope and I put on the first Leatherman’s Loop race.  We greeted the ninety runners who trusted that we knew what we were doing and showed up to race our course. Trail running races in those days were few and far between and necessitated long drives and early starts. It pleases me to see that interest in running and racing on non-paved surfaces has really taken hold. At the bottom of this note I will list five trail races in Westchester and Fairfield counties which are coming up this fall.

The team of organizers and directors (currently Rob and Mike and Judy and Tony) who bring you the Leatherman’s Loop each year have no big changes in mind. Four years ago we added the Run the Farm five miler and as of right now, we have no plans to add any additional races. By choice, both races have always been and will continue to be staged without any corporate sponsorship. That being said, you the runners cover all expenses through your entry fees and we still are able to make generous charitable donations.

My fall running plans are to participate in all five of the races listed below. My hope is that many of you will choose to join me.


Where the Pavement Ends

Sunday 09/22/13
Tri Ridgefield
Lake Windwing Ridgefield Ct.
4 miles mostly single track

Sarah Bishop Bushwhack

Sunday 09/29/13
Leatherman Harriers Sunday Runners
Mountain Lakes Park North Salem N.Y.
10K mostly single track
1.5 mile kids race

Paine to Pain

Sunday 10/06/13
New Ro Runners
Thomas Paine cottage New Rochelle N.Y.
13.1 miles with some pavement

Run the Farm

Sunday 10/27/13
Leatherman Harriers
Muscoot Farm Somers N.Y.
5 miles all trails
1.1 miles for kids 7 through 12
0.6 miles for kids 6 and younger

Back Country Bushwhack

Sunday 11/10/13
Threads and Treads
Camp Simmons Greenwich Ct.
4 miles with water crossings


Sarah Bishop Bushwhack 10k Open for Registration!

Sarah Bishop Bushwhack

Trail Runners:

We are pleased to announce our Sunday Runs group has organized a new trail race – The Sarah Bishop Bushwhack 10k! Registration is open now.

The Sarah Bishop Bushwhack is a unique and challenging 10K trail race in Mountain Lakes Park, Northern Westchester, New York, held on Sunday, September 29, 2013, at 9:15am.

Just a few miles north of the Leatherman’s Loop site and easily drivable from New York City and Connecticut, the course traverses through the park’s over 1000 acres of scenic woodlands, beautiful vistas, and around the lakes that give the park its name. See the course map here ››

If you’re familiar with the Leatherman’s Loop trail race, then you know how fun and challenging the terrain in Northern Westchester can be. This course passes Lookout Point overlooking Lakes Waccabuc, Rippowam, and Oscaleta then goes over Bailey Mountain (at 982 feet, the highest point in Westchester) before touching the Connecticut border and finishing near Hemlock Lake.

Along the way, you’ll traverse single-track narrow trails and wider abandoned carriage roads that are perfect for picking up some speed. There are seasonal streams that that you’ll cross but nothing too deep. Still, with 1000 feet of overall elevation gain in the 10k race, there are plenty of challenging hills to make things interesting.

If you’ve run the Leatherman’s Loop, you’ll understand why we like to say that Sarah Bishop is hairier than the Leatherman. Sarah Bishop lived during the Revolutionary War and was famous before The Old Leather Man – read about her local legend here. We’d like to think if they had known each other they would have been  friends. You may notice they even look alike… 

The race is limited to 400 participants and will fill up quickly so register early. Sarah’s Scramble, a tough 1.5 mile kids’ race is also open on a limited basis.

Come out and experience Mountain Lakes Park and run in the woods that Sarah Bishop called home.

Hope to see you on the trails!

-The Sunday Run Crew

Run The Farm 2013 Registration Open


Run The Farm 2013 trail races are open for registration.

The races are set for Sunday, October 27, 2013 at Muscoot Farm on Route 100 in Katonah/Somers, NY.

The main event is the 5 mile trail race. Afterwards there is a farmers market, live music, and awards.

New for 2013 – We have separated the kids races. We will hold a 2k race for 7-12 year olds and a 1k race for 6 year olds and younger. Separate start times and finishes – see website for details.

Hope you can come!

4th Annual Run The Farm – October 27th, 2013

The fourth annual Run The Farm trail races are set for Sunday, October 27, 2013 at Muscoot Farm on Route 100 in Katonah/Somers, NY.

There will be two separate kids races, a 2k race for 7-12 year olds and a 1k race for 6 year olds and younger. The main event is the 5 mile trail race. Afterwards there is a farmers market, live music, and awards.

Visit runthefarm.org for more information. Hope you can come!