Skip to main content
triboutique.ca - Triathlon gear with free shipping over $125 triboutique.ca - Free shipping over $125 with coupon code CANADA: Triathlon Equipment, wetsuits, Swimskins and gifts.

John Jay Community Trail Race

Date:
Sun, Apr 12, 2026 at 9:00 AM – 10:00 AM
Location:
40 N Salem Rd
Town of Lewisboro, New York
10518
United States
OpenStreetMap Google Maps
Links:
jjtrail.org Register at runsignup.com
Tags:
4k 5k Run Trail Walk

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.]

More races nearby

  • 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.
    1.1 km from Town of Lewisboro
    Reservation Road, Town of Lewisboro, New York, 10518, United States
    OpenStreetMap Google Maps

    10k Run Trail

  • Try the Trail [runsignup.com]

    Sun, Apr 26, 2026 at 9:00 AM

    Description

    Get ready to hit the trails and have some fun! The Try the Trail youth trail run is a family-friendly event designed for kids and teens ages 4 to 16 who want to enjoy running outdoors on scenic...

    Get ready to hit the trails and have some fun! The Try the Trail youth trail run is a family-friendly event designed for kids and teens ages 4 to 16 who want to enjoy running outdoors on scenic trails at Katonah Memorial Park.

    Participants can choose the distance that’s right for them:

    • Half-Mile Run - 1 loop around the course

    • Full-Mile Run - 2 loops of the course

    The trail course is easy to follow and perfect for beginners and young runners looking to try something new. Whether your child is racing for time or just enjoying the fresh air and movement, this event is a great way to build confidence, stay active, and have fun in a supportive, positive environment.

    Come run, explore, and enjoy the trail!
    6.9 km from Town of Lewisboro
    38 High Street, Town of Bedford, New York, 10536, United States
    OpenStreetMap Google Maps

    1 Miles Run Trail

  •  Run Like a Mother 5K and Kid's 1-Mile 2026 [runlikeamother.com] [Register at runsignup.com]

    Sun, May 10, 2026 at 8:00 AM

    Description

    Run Like a Mother 2026 🌸

    Women’s 5K & Kids 1-Mile

    📍 Ridgefield, Connecticut

    🗓 Sunday, May 10, 2026

    Kids 1-Mile – 8:00 AM

    Women’s 5K – 8:30 AM

    Mother’s Day in Ridgefield means one thing — Run Like a...

    Run Like a Mother 2026 🌸

    Women’s 5K & Kids 1-Mile

    📍 Ridgefield, Connecticut

    🗓 Sunday, May 10, 2026

    Kids 1-Mile – 8:00 AM

    Women’s 5K – 8:30 AM

    Mother’s Day in Ridgefield means one thing — Run Like a Mother is back!

    Celebrate the incredible women in your life (or yourself!) with a joyful, high-energy morning filled with movement, community, and fun. Whether you're chasing a PR or jogging with friends, this welcoming 5K is perfect for beginners and seasoned runners alike.

    The scenic course kicks off at The Ridgefield Playhouse and finishes in beautiful Ballard Park, where the celebration continues!

    Expect:

    • A supportive, all-women race atmosphere

    • Families lining the streets cheering you on

    • A festive finish-line celebration

    • Runner refreshments

    • A fun-filled kids’ activity area

    • Smiles, memories, and Mother’s Day magic

    • Bring the whole family — the kids can race in the 1-Mile before lining the course to cheer Mom to the finish!

    Make it your new Mother’s Day tradition.

    Run. Celebrate. Inspire.
    9.5 km from Town of Lewisboro
    80 East Ridge, Ridgefield, Connecticut, 06877, United States
    OpenStreetMap Google Maps

    1 Miles 3.1 Miles 5k Run

  • TRI the PARK [runsignup.com]

    Sun, Jun 07, 2026 at 8:00 AM

    Description

    Date: Sunday, June 7th, 2026 at 8:00am

    Join us for TRI the PARK at Bedford Hills Memorial Park, a youth triathlon designed for fun, challenge, and community spirit! Participants will compete in a...

    Date: Sunday, June 7th, 2026 at 8:00am

    Join us for TRI the PARK at Bedford Hills Memorial Park, a youth triathlon designed for fun, challenge, and community spirit! Participants will compete in a POOL swim, followed by a park bike and run. Whether your athlete is tackling the long course or giving the short course a go, it’s a great way to race into summer.

    The entire race should take athletes anywhere from 10 to 30 minutes as it is a beginner course, and each participant will receive a finisher’s medal!

    Long Course: 100m swim, 2mi bike, 0.50mi run

    Short Course: 50m swim, 1mi bike, 0.25mi run

    Participants can compete in either distance race and must be between the ages of 6-16.

    Register by noon on May 10th to guarantee your event T-shirt! After that, shirts will be available on a first come, first served basis while supplies last. Registration closes on May 31st.
    9.6 km from Town of Lewisboro
    60 Haines Road, Town of Bedford, New York, 10507, United States
    OpenStreetMap Google Maps

    Run Swim Triathlon

  • Ridge Reaper Trail Runs [steependurance.com] [Register at ultrasignup.com]

    Sat, Aug 01, 2026

    1.3 km from Town of Lewisboro
    Meadow Parking Lot, Town of Lewisboro, New York, 10518, United States
    OpenStreetMap Google Maps

    25k 50k Run Trail Ultra

More races nearby →
Like Wikipedia, anyone can contribute. Sign up to add your local events.