Hat City Dash

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.

Run or walk this 5K to support Ann's Place then kick back and enjoy one of Connecticut’s best post-race parties! Unwind and enjoy an outdoor barbecue, ice cold beer, refreshments, DJ and an awards ceremony. Bring your favorite picnic blanket or folding chair and enjoy the beautiful grounds of the Amber Room for the after-race celebration.

This is an important fundraiser for Ann’s Place cancer support services. All proceeds go directly to Ann’s Place and help keep our doors open and our cancer support services FREE of charge to all those in need in our community. www.annsplace.org

It’s easy and fun to fundraise! Create your own fundraising page or create a team page. Have some team building with your colleagues or friends or set your own personal goals. Waterworks, our presenting sponsor has friendly competitions between teams and have worn costumes to encourage donations. Other teams have created custom shirts and/or raised money in honor of someone, so many great ideas! We can't wait to see what everyone comes up with this year!

Want to join in on the social media fun? Share your pictures and videos, while in training and during the race, via social media using the hashtag #runfromthesun5K

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.

Ready, Set, RACE!

Join us for the first annual New Pond Farm Hayfield Hustle! Choose from a scenic 5 mile, 5k, or Children's Sap fun run through the hayfields and byways of New Pond Farm, all finishing with a rollicking family-friendly Oktoberfest celebration. Races benefit New Pond Farm Education center, a nonprofit dairy farm of distinction and environmental education center. We educate and inspire each generation to become stewards of the land by championing conservation and sustainable farming practices to protect and preserve our natural world.

The 5 mile race features gentle hills along rolling pastures, with waterfall views as you pass the Mark Twain Library, and finishes with a dash through our dairy barn.

The 5K begins through the picturesque farmland, includes some challenging hills along winding country roads, and finishes with a fast and easy downhill run through our dairy barn.

The Children's Sap run highlights the stream, pond, and animals of New Pond Farm, and will be untimed.

Participants are welcome at all paces, including walkers. Jogging strollers are only allowed on the 5k course.

Race registration includes entry into our family friendly Oktoberfest, which includes live music, a scavenger hunt throughout the 102 acres of pasture and woodlands, games, hay rides, and of course frosty beer. Food will be available for purchase.

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.