Southwest Cafe Margarita 5K

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.

It began with Lt Col Dan Rooney’s flight home from his second tour of duty in Iraq. An F-16 fighter pilot in the Oklahoma Air National Guard, he became painfully aware of the realities families face when a loved one in uniform is fallen or disabled.

As his flight landed, the pilot announced they carried the remains of Corporal Brock Bucklin on board. Lt Col Rooney watched as Corporal Bucklin’s twin brother walked somberly alongside the flag-covered casket to meet his family on the tarmac. Among them was the deceased Corporal’s young son, Jacob.

Since that night, Lt Col Rooney has committed his life to rallying patriotic Americans and meeting sacrifice with hope through the Folds of Honor. Since 2007, Folds of Honor has provided life-changing scholarships to the spouses and children of fallen or disabled military and first responders. On our watch, those who protect our freedoms and our families will know they are not forgotten.