The Ridgefield Road Fest 50th ANNIVERSARY: 1/2 Marathon, 7-Miler, & Iris Fund 5K

More races nearby

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

  Sun, Apr 12, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  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.]

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

  4k 5k Run Trail Walk

•  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

  ▼ Show more Show less

  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.

  2.2 km from Ridgefield
  80 East Ridge, Ridgefield, Connecticut, 06877, United States
  OpenStreetMap Google Maps

  1 Miles 3.1 Miles 5k Run

• TriRidgefield Sprint Triathlon and Duathlon [runsignup.com]

  Sun, May 31, 2026 at 7:00 AM

  Description

  ▼ Show more Show less

  We are pleased to present TriRidgefield and DuRidgefield. First held in 2007, the races wind their way through the bucolic countryside of Ridgefield, Connecticut. There will be a Sprint Triathlon,...

  We are pleased to present TriRidgefield and DuRidgefield. First held in 2007, the races wind their way through the bucolic countryside of Ridgefield, Connecticut. There will be a Sprint Triathlon, consisting of a half-mile swim in pristine Great Pond, a rolling 13-mile bike ride, and a challenging 5K finishing run. For you non-swimmers, we will also have a Sprint Duathlon held concurrently with the Tri, consisting of a 2-mile run, followed by the same 13-mile bike ride, and finishing 5K run.

  NOTE: For registrations received after May 1, we cannot guarantee you will receive a shirt.

  3 km from Ridgefield
  19 Great Pond Road, Ridgefield, Connecticut, 06877, United States
  OpenStreetMap Google Maps

  Duathlon Run Sprint Swim Triathlon

• Hat City Dash [runsignup.com]

  Sun, Jun 07, 2026 at 9:30 AM

  Description

  ▼ Show more Show less

  This race will start and finish on Kenosia Avenue. Runners will begin the race heading northbound until they reach Christopher Columbus Avenue. From there, runners will continue around the cul-de-sac...

  This race will start and finish on Kenosia Avenue. Runners will begin the race heading northbound until they reach Christopher Columbus Avenue. From there, runners will continue around the cul-de-sac and head back towards the start/finish line. The course is flat and will have a hydration table set up around the halfway point. There will be a post race party and awards at Elicit Brewery following the race.

  Every dollar raised from this race will go toward supporting an officer’s child’s higher education fund. At the end of the event, a recipient will be randomly chosen by an independent third party.

  A free beer from Elicit Brewing will be given to any runner age 21+, with valid proof of sign up.

  There will be plenty of parking available on race day at the Elicit Brewery lot, located at 15 Backus Avenue.

  Early bib pickup will be available on Saturday, June 6th at Elicit Brewery

  9.2 km from Ridgefield
  15 Backus Avenue, Danbury, Connecticut, 06810, United States
  OpenStreetMap Google Maps

  3.1 Miles Run

• Southwest Cafe Margarita 5K [runsignup.com] [Register at runsignup.com]

  Sat, Jul 25, 2026 at 7:00 PM

  Description

  ▼ Show more Show less

  THE summer race with the best way to cool down, a margarita of course!

  Barbara Nevins and Southwest Cafe present the 20th annual Southwest Cafe Margarita 5k to benefit Ability Beyond. The yummy...

  THE summer race with the best way to cool down, a margarita of course!

  Barbara Nevins and Southwest Cafe present the 20th annual Southwest Cafe Margarita 5k to benefit Ability Beyond. The yummy margarita you know and love will be waiting for you at the post-race fiesta! Race begins at 7pm!

  The Southwest Cafe Margarita 5K continues to support Ability Beyond, an organization dedicated to empowering every person, no matter their ability, to live, work and thrive as members of their community. The non-profit currently runs two residential programs in Ridgefield: Sunrise Cottage and Ritch Drive. Click on the "donation" button to find out more about Ability Beyond.

  1.6 km from Ridgefield
  109 Danbury Road, Ridgefield, Connecticut, 06877, United States
  OpenStreetMap Google Maps

  3.1 Miles 5k Run