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Date:
Sun, Nov 01, 2026 at 12:00 AM – 11:59 PM
Location:
Reservation Road
Town of Lewisboro, New York
10518
United States
OpenStreetMap Google Maps
Links:
ravenrocksrun.org Register at runsignup.com
Tags:
10k Run Trail Ultra Virtual Walk

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!).

More races nearby

  • 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.]

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

    4k 5k Run Trail Walk

  • 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.

    0 m 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!

    6.1 km from Town of Lewisboro
    38 High Street, Town of Bedford, New York, 10536, United States
    OpenStreetMap Google Maps

    1 Miles Run Trail

  • BCSD Elementary Bike Run [runsignup.com]

    Sun, May 17, 2026 at 8:00 AM

    Description

    Registration will be open from Monday March 16, 8:00am through Sunday March 22.

    Mandatory race packet pickup outside the Fox Lane Middle School from 8:00 - 11:00 a.m. on Saturday, May 16.

    The event...

    Registration will be open from Monday March 16, 8:00am through Sunday March 22.

    Mandatory race packet pickup outside the Fox Lane Middle School from 8:00 - 11:00 a.m. on Saturday, May 16.

    The event is at 8 a.m. on Sunday, May 17.

    Distances

    • 4th-5th Grade: 5 bike laps (2 miles), 4 run laps (1 mile)

    • 2nd-3rd Grade: 3 bike laps (1.2 miles), 2 run laps (.5 mile)

    • K-1st Grade: 2 bike laps (4/5 mile), 1 run lap (1/4 mile)

    With an exception for children with special needs, all children will be required to bike or scoot AND run the course.

    9.4 km from Town of Lewisboro
    632 S Bedford Rd, Town of Bedford, New York, 10506, United States
    OpenStreetMap Google Maps

    Duathlon 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.

    8.7 km from Town of Lewisboro
    60 Haines Road, Town of Bedford, New York, 10507, United States
    OpenStreetMap Google Maps

    Run Swim Triathlon

More races nearby →

Local running group

  • [runningcrews.com] [runningcrews.com] - Facebook - Instagram

    The Boogie Down Bronx Runners are a vibrant and inspiring collective founded on May 30, 2017, with a powerful mission to bring a community-focused running culture to their home borough. Established by founders Lenny and Jean Paul, the crew was created to fill a void and promote wellness and engagement for people of all abilities. From a first run of just three people, they have grown into a major force in the New York City running scene, embodying their motto, "All for our borough!" with every stride they take.

    Community Run

    New York, New York, United States
    OpenStreetMap Google Maps
See all organizations →
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