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  • John Jay Community Trail Race [jjtrail.org] [Register at runsignup.com]

    Sun, Apr 12, 2026 at 9:00 AM

    Description

    SPONSORS

    Thank you to our wonderful sponsors! We are always looking for additional sponsors for the community races! We truly appreciate the sponsors who enable us to host a fun and competitive race...

    SPONSORS

    Thank you to our wonderful sponsors! We are always looking for additional sponsors for the community races! We truly appreciate the sponsors who enable us to host a fun and competitive race event.

    We are seeking sponsors for the 2026 races. If you are interested in sponsoring or renewing your sponsorship, please contact us at jjtrailrace@gmail.com.

    A listing of the current year's sponsors is here: https://runsignup.com/Race/Sponsors/NY/CrossRiver/JohnJayCommunityTrailRace or click on the "Sponsor" link above. We will reset this list and update with new sponsors in the months before the next race.

    You can see all of our past year's sponsors (thank you!!) at our https://jjtrail.org/sponsorship link.

    We could not put on the event without our SPONSOR PARTNERS -- and we encourage everyone to patronize them!

    DONORS

    Thank you to our generous donors who have helped us build the trail, bridges, and boardwalks. More work is needed! Add your name to the list while we are fundraising here: runsignup.com/jjtrail/donate.

    THE RACE

    The John Jay Community 5k Trail Race (http://jjtrail.org) is a competitive community race on the new John Jay Community Cross Country Trail. The course starts on the lower fields of the John Jay Campus and quickly goes into the wooded trails adjacent to the middle school and high school. It ends on the John Jay Contest Track & Field next to Route 121. The trails are challenging and hilly in the woods.

    The John Jay 4k Trail Walk is a non-competitive walk through the main parts of the John Jay Community Trail. The walkers will start after the 5k runners are in the woods. Most of the trail is the same except for approximately 1k of the southern hill loop that is skipped by the walkers.

    Both courses end at the John Jay Contest Field.

    Note: since the trail and course is on school grounds, animals are not permitted - except for service animals within the ADA definition.

    Sign up NOW - first 150 pre-registered runners/walkers to sign up receive a race t-shirt!

    The Kids Jay Dash race will take place after the finish of the 5k run/4k walk. It will be held on the track and the distance will be 200 meters. The first 30 kids to sign up for the Dash will receive a t-shirt!

    TRAIL BUILDING

    The John Jay Community Cross Country Trail has been developed and built by student and community volunteers to provide a home course for the Westchester County and New York State Championship John Jay Cross Country teams as well as for the community. If you are interested in helping out, either via donation or volunteering your time, please reach out to us at jjtrailrace@gmail.com for more information. Thank you!

    [RACE DAY REGISTRATION, IF AVAILABLE, STARTS AT 7:30am at the JJMS FIELD on race morning.]

    20.3 km
    40 N Salem Rd, Town of Lewisboro, New York, 10518, United States
    OpenStreetMap Google Maps

    4k 5k Run Trail Walk

  • Roxbury Road Race Series #8 [runsignup.com]

    Sat, Apr 25, 2026 at 8:30 AM

    Description

    4.7 Miles- Down Squire, Highbridge, Up Jeep Trail

    Active duty military/veterans and active first responders are encouraged to contact the race for a discount.

    24.1 km
    18 Apple Lane, Northwest Hills Planning Region, Connecticut, 06783, United States
    OpenStreetMap Google Maps

    4.7 Miles Run Trail

  • Leatherman's Loop [leathermansloop.org] [Register at runsignup.com]

    Sun, Apr 26, 2026 at 9:00 AM

    Description

    The Leatherman's Loop is put on by Leatherman's Loop Races.

    Other races include: SPRING Run the Farm (May 17, 2026) • FALL Run the Farm (Oct 25, 2026) • Raven Rocks Run (Nov 9, 2025) •


    The...

    The Leatherman's Loop is put on by Leatherman's Loop Races.

    Other races include: SPRING Run the Farm (May 17, 2026) • FALL Run the Farm (Oct 25, 2026) • Raven Rocks Run (Nov 9, 2025) •


    The Leatherman's Loop is a 10k trail race held in the spring (April 26, 2026). Start time is 9am. (ARRIVE at the park BY 8AM if you are registered to run!)

    If you have questions about the race, visit the Loop website or specifically the Loop FAQ page at the website.

    You can follow us on Instagram: https://instagram.com/leathermansloop and Facebook: https://facebook.com/leathermansloop

    Due to the popularity of the event, Loop entry is via Lottery. For more information, visit our Loop Lottery FAQ page here.

    We are always grateful to our race volunteers! If you'd like to sign up to volunteer, visit this page: https://leathermansloop.org/volunteer

    Please put leathermansloop@gmail.com and info@runsignup.com in your address book so our emails to you and the confirmation emails from RunSignUp.com do not get tagged as spam.

    Thanks!

    -Rob, Ciorsdan, and the Leatherman Harriers volunteers

    PS: two additional notes:

    1.) The registration cost of the Leatherman's Loop incorporates the park's entry fee into the registration cost -- so the park does not have to collect the parking fee separately from each entrant on race morning. Long ago we figured out it was more efficient for us to pay the park that fee directly rather than have hundreds of cars line up at the entrance fumbling for cash at the entrance gate to the Rez on race morning.

    2.) Dogs are not permitted to run in the Loop. In 2020 the USATF began a new policy prohibiting dogs from running in races they sanction and insure. The Loop is a USATF sanctioned and insured race. Leashed dogs are welcome at the park anytime.

    21.3 km
    Reservation Road, Town of Lewisboro, New York, 10518, United States
    OpenStreetMap Google Maps

    10k Run Trail

  • Forgotten Forest Ultra Run [rooseveltforestultras.com] [Register at ultrasignup.com]

    Sat, May 16, 2026 at 8:30 AM

    23.5 km
    700 Peters Lane, Stratford, Connecticut, 06614, United States
    OpenStreetMap Google Maps

    Run Ultra

  • Roxbury Road Race Series #13 [runsignup.com]

    Sat, May 30, 2026 at 8:30 AM

    Description

    3.9 Miles- Jeep Trail

    Active duty military/veterans and active first responders are encouraged to contact the race for a discount.

    24.1 km
    18 Apple Lane, Northwest Hills Planning Region, Connecticut, 06783, United States
    OpenStreetMap Google Maps

    3.9 Miles Run Trail

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