Races

Run Like a Mother ® Virtual 5K & Kids 1 Mile   The mission of Run Like A Mother® is to fuel a woman's journey through health and wellness, empower with education and training programs, inspire with communities, events and races, and enable through programs and partnerships. Run Like A Mother ® isn't just a Race, it’s our way of life. We are every woman, from every walk or run of life, gathering together (virtually) to encourage a healthy lifestyle through moving. On Mother’s Day weekend, we celebrate who we are and what we do.  Whether you are a mother or not, we understand the importance of modeling healthy behaviors for our future generations.  Most importantly, it is the caring of our own bodies and minds that make us stronger every day.

Run Like a Mother 2026 🌸Women’s 5K & Kids 1-Mile📍 Ridgefield, Connecticut🗓 Sunday, May 10, 2026 Kids 1-Mile – 8:00 AMWomen’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 atmosphereFamilies lining the streets cheering you onA festive finish-line celebrationRunner refreshmentsA fun-filled kids’ activity areaSmiles, memories, and Mother’s Day magicBring 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.

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.

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.

Where the Pavement Ends Trail Races are set for Sunday, September 20, 2026                             You can do one loop of the course or do two loops for a “Pavement Double”!   The race starts and ends at Lake Windwing ballfields in Ridgefield, CT. The 4.25-mile course (single loop) begins at 7:30 AM, and the 8-miler (approximate double loop) begins at 7:00 AM. The course runs through the Hemlock Hills/Pine Mountain open space areas. It's technical, rocky, and sublime. If you are not an experienced trail runner, we recommend choosing the 4.25-mile course.   This race is part of the Trail Mix Series—Westchester-Fairfield Trail Mix Series: a series of seven trail races. The results from all the races are combined to determine a series winner and award special prizes.

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, Educatio