Skip to main content
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 [email protected].

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 [email protected] for more information. Thank you!

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

More races nearby

  • 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

  • Pound Ridge 5k and Kids Dash [townofpoundridge.gov] [Register at raceroster.com]

    Sun, Jun 28, 2026 at 9:00 AM

    Description

    28th Annual Road Race & 250th Anniversary of USA

    Celebrate the 250th anniversary of the United States with a community tradition! Join us on Saturday, July 4th, 2026, for a morning of fitness,...

    28th Annual Road Race & 250th Anniversary of USA

    Celebrate the 250th anniversary of the United States with a community tradition! Join us on Saturday, July 4th, 2026, for a morning of fitness, family, and fun.

    Race Schedule & Details

    Event

    Age Group

    Start/Check-In Info

    5K Road Race

    All Ages

    Starts at Pound Ridge Elementary at 9:00 AM. (Check-in starting at 8 AM)

    1K Run

    Ages 7–13

    Check-in at Elementary School at 8 AM for busing to the start line.

    Kids Dash

    Ages 2–6

    Check-in at Pound Ridge Town Park at 9:30 AM. The race begins after the 5K.

    Registration & Pricing

    Save money by signing up early! Please note that race-day registrations are cash only.

    • 5K Race: $25 Pre-Race | $30 Day-of (Cash)

    • 1K Race: $15 Pre-Race | $20 Day-of (Cash)

    • Kids Dash: $10 Pre-Race | $10 Day-of (Cash)

    Swag & Post-Race Perks

    Every participant is a winner! All runners will receive:

    • Official Road Race T-Shirt: Please wear this during your run!

    • Commemorative Pint Glass: To be collected at the finish line.

    • Face Painting for kids!

    The Celebration:

    After you cross the finish line at Pound Ridge Town Park, stick around for a light continental breakfast and refreshments generously provided by Ridgefield Bagels.

    Important Logistics

    • 5K Finish Line: The race concludes at Pound Ridge Town Park.

    • 1K Transportation: 1K participants must check in at the Elementary School to be bused to the Beech Hill insertion point.

    • Kids Dash Location: This event takes place entirely within the Town Park.

    Bib-pick up will be available the day of the race or on Thursday July 2nd at Townhouse (179 Westchester Ave, Pound Ridge, NY) from 11:00 a.m.-3:00 p.m. In person registration on this day as well.

    7.1 km from Town of Lewisboro
    7 Pound Ridge Road, Town Of Pound Ridge, New York, 10576, United States
    OpenStreetMap Google Maps

    1k 5k Kids Run

  • 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

  • The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 Marathon, 7-Miler, & Iris Fund 5K [runsignup.com]

    Sun, Oct 18, 2026 at 7:15 AM

    Description

    October 18, 2026

    Ridgefield Half-Marathon 7:15 AM

    Ridgefield 7-Miler 7:15 AM

    Iris Fund 5K 7:30 AM

    These races feature classic fall New England scenery. The races are beginner-friendly, and you will...

    October 18, 2026

    Ridgefield Half-Marathon 7:15 AM

    Ridgefield 7-Miler 7:15 AM

    Iris Fund 5K 7:30 AM

    These races feature classic fall New England scenery. The races are beginner-friendly, and you will run through some of the prettiest roads in Fairfield County! The race starts on East Ridge Road, just above The Boys and Girls Club of Ridgefield, with a few gradual climbs to keep you honest. It then settles into a nice rolling course that winds through southern Ridgefield for two loops that showcase some of the flattest miles in the town. With a fast downhill into downtown Ridgefield and back to the Boys and Girls Club, where you're sure to finish strong and smiling!

    This race’s primary benefactor is the Boys & Girls Club of Ridgefield. The Boys & Girls Club of Ridgefield is a national award-winning youth activity center designed to offer programs for school-aged children after school and during vacations in five core areas: The Arts, Character & Leadership, Education, Health & Life Skills, and Sports, Fitness & Recreation.

    The 5K proudly supports The Iris Fund, founded in loving memory of Iris Crystal Aleman. Dedicated to ending the heartbreak of prematurity, the Fund fuels research into the triggers of labor and supports families facing high-risk pregnancies and loss.

    Everyone who donates $10 or more to the Boys & Girls Club through the registration platform (RunSignUp) will be entered into a raffle for some great prizes! Donating $25 will get you two entries. We will be raffling off items to be announced at a later time.

    9.6 km from Town of Lewisboro
    Ridgefield, Connecticut, 06877, United States
    OpenStreetMap Google Maps

    3.1 Miles 5k 7 Miles 13.1 Miles Half Marathon Run

  • Raven Events [ravenrocksrun.org] [Register at runsignup.com]

    Sun, Nov 01, 2026 at 12:00 AM

    Description

    The Raven Rocks 10k Trail Run is BACK for NOVEMBER 8, 2026! Woo hoo!

    We have also brought back the 100k Raven Challenge with all of the fun elements from last year -- plus we're looking to add a few...

    The Raven Rocks 10k Trail Run is BACK for NOVEMBER 8, 2026! Woo hoo!

    We have also brought back the 100k Raven Challenge with all of the fun elements from last year -- plus we're looking to add a few more activities to the challenge during the month of November!

    You can sign up for one or the other -- or do BOTH! Signups for both events at the same time get a discount which appears at checkout.

    Shirts this year are one design and available either on long-sleeved cotton shirts (traditional) and/or short sleeved tech fabric shirts (new!). You can purchase one, both, or neither shirt. If you are a purely virtual Raven 100k Challenge runner, we will mail you your shirt if ordered along with your finisher woodallion.

    As always, these Raven events support the Friends of Trailside Museum and Ward Pound Ridge Reservation. During registration we encourage runners and challengers to join as members of the museum to support their non-profit educational and conservation purpose.

    Once the donation vehicle has been established, we will support the Friends of the Cross River Mountain Fire Tower. We are working with the Westchester Parks Foundation who plan to raise funds to support Westchester County and NY State in the restoration of the fire tower to Ward Pound Ridge Reservation. That fundraising account will be set up soon with a range of support levels. More news to come!

    More information about each event

    Raven Rocks Run - 10k Trail Run

    The Raven Rocks Run is a challenging 10k trail run at Ward Pound Ridge Reservation in Cross River, NY.

    The ELEVENTH running of the race will be in November.

    Race will be in-person Sunday, November 8, 2026 starting at 9am. (Final race date approval pending county permit.)

    The race will start in the Meadow near the fallen oak tree and its massive remains. The course passes by the spot where the Leatherman’s Loop begins. Instead of heading towards the river as the Loop does, the Raven Rocks Run 10k course climbs and climbs up to the two highest points in the park (Raven Rocks Overlook and the Fire Tower Summit) before heading back for a (mostly) downhill and (relatively) flat finish.

    The course passes by the site of the former Blue Trail fire tower which is the highest point in the park. We are working towards getting back the tower to its former spot in the park. See Course Map page for course details.

    More information about the race and tower project is on the About page and the FAQ page of our ravenrocksrun.org website.

    We are looking forward to November when we will run this event for the ELEVENTH time!

    Important: Our Raven Rocks Run race plans are contingent on permit approval from the Westchester County Department of Parks, Recreation, and Conservation. This approval is not guaranteed but has been obtained for the prior nine races. As in all prior years we open registration with the understanding that the race will take place. We will update runners if the permit is not approved for the current year.

    Raven 100k Challenge

    The Raven 100k Challenge is simple: first, register for the challenge. Then run, hike, or walk 100k during the month of November 1st - 30th, 2026.

    Note: You can register as late as November 15 for the 100k challenge and enter your mileage to date when you register.

    This works out to an average of around 3k per day or 25k (15 miles) per week.

    If you complete the challenge, you will receive a wooden finisher medallion. Shirts are optional.

    The Raven 100k Challenge supports the Friends of Trailside Museum and Ward Pound Ridge Reservation, a 501(c)3 not for profit organization based at the Trailside Museum at Ward Pound Ridge Reservation.

    You can also join the Friends of Trailside Museum and Ward Pound Ridge Reservation for annual membership during signup.

    Bonus achievements

    In addition to running, walking, or hiking 100k during November, there are several bonus achievement badges you can unlock if you are able:

    • Run 10k on the Raven Rocks Run course (raven badge)

    • Run 5x 10k on the Raven Rocks Run course (ultra raven badge - subs out the raven badge when this badge is achieved)

    • Run 10x 10k on the Raven Rocks Run course (flock badge - subs out the ultra raven badge when this badge is achieved)

    • Take a selfie at the Raven Rocks Overlook and send it in (photographer badge)

    • Submit a photo of yourself on a run with your "I Voted" sticker or if you can't vote in the election, next to someone with an "I Voted" sticker. Or simply log a run, walk, or hike on election day! (bald eagle badge)

    • Submit a photo of you running on Thanksgiving. Or simply log a run, walk, or hike on Thanksgiving. (turkey badge)

    • Submit a photo of you running on Veteran's Day. Or simply log a run, walk, or hike on Veteran's Day. (veterans day badge)

    • Photo of a raven or Raven related site, store, zoo, etc. and send it in (raven citizen award)

    • Do a run in the dark to Raven Rocks (night owl badge)

    • 200k distance in November (snowy owl badge)

    • 300k distance in November (white raven badge)

    • Run the Raven Rocks 10k course 5x IN ONE DAY (Raven Rockstar Badge)

    • Run the Raven Rocks 10k course 32 times in November (Peeter Badge)

    • Witness a meteor falling during a run (Meteor Badge)

    • Read a stanza from Edgar Allan Poe's "The Raven" poem and send us a link. Use soundcloud, youtube, facebook, whatever service you want. (wise owl badge)

    • These badges will be displayed on the physical wooden finisher "medallion" once you complete the Raven Challenge. We will also show badges achieved on the summary page.

    • Any other badge ideas? We are open to suggestions :)

    In addition, we will have recognition for:

    • First 3 men and First 3 women to 100k

    • Top 3 men and Top 3 women in total kilometers.

    • Anyone in contention for these Top 3 awards must make their entries in a timely manner:

    • All entries must be made within 36 hours of your run/walk.

    • If you do not enter your results within 36 hours you will not be eligible for any "Top 3" challenge recognition. We want our top participants to be in a 'virtual race' with each other. Without timely distance entries, this is not possible.

    • This is to discourage participants from "batch entering" their results and leaping to the top or near the top of the standings.

    • Keep your results up to date if you are in the running!

    • Note: In order to win these awards distance submissions need to be made via GPX files.

    • See instructions submitting results on RunSignUp Raven 100k Challenge page.

    HALFWAY (50K) bonus search

    For those in the area near Ward Pound Ridge Reservation we have a special treat in mind. If you opt-in via the badge update form (AFTER you pass the 50 kilometer mark on your Raven 100k Challenge) we will send you GPS coordinates to somewhere in the park where we have hidden a small challenge surprise for you to find. It will be obvious once you get there, but not easy to find unless you have the coordinates. Complete instructions and advice come with the GPS challenge confirmation email.

    Everyone will have a different and unique spot somewhere in the park. Some will be further off-trail than others depending on how familiar you are with the park. You can ask for harder or easier location in the request and we will do our best to accommodate your request! Difficulty estimates can be subjective though!

    Let us know when you find your halfway bonus (or if you can't find it!).

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

    10k Run Trail Ultra Virtual Walk

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