Run in Ridgefield, Connecticut | 2026-2027

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.

1 Miles 3.1 Miles 5k Run

80 East Ridge, Ridgefield, Connecticut, 06877, United States
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TriRidgefield Sprint Triathlon and Duathlon [runsignup.com]

Sun, May 31, 2026 at 7:00 AM

Description

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.

Duathlon Run Sprint Swim Triathlon

19 Great Pond Road, Ridgefield, Connecticut, 06877, United States
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Southwest Cafe Margarita 5K [runsignup.com] [Register at runsignup.com]

Sat, Jul 25, 2026 at 7:00 PM

Description

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.

3.1 Miles 5k Run

109 Danbury Road, Ridgefield, Connecticut, 06877, United States
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Where the Pavement Ends Single & Double Loop [runsignup.com]

Sun, Sep 20, 2026 at 7:00 AM

Description

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...

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.

4.3 Miles 8.2 Miles Run Trail

South Shore Drive/Lake Windwing, Ridgefield, Connecticut, 06877, United States
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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.

3.1 Miles 5k 7 Miles 13.1 Miles Half Marathon Run

Ridgefield, Connecticut, 06877, United States
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5 running events in Ridgefield, Connecticut

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Local Clubs & Organizations