Falling for Fairfield County Road Races


Global Running DayNew England has some of the best temperatures and courses for fall road races. Fairfield County boasts several road races ranging from beginner to moderate and more challenging. It’s a great way to take in a fall weekend afternoon through the foliage and hills. Most also offer family-friendly kids race options as well. I’ve rounded up a list of some annual local races offering both in-person and virtual race options throughout the next two months. Happy jogging runners!

September 18 {Easton}

The Easton Police Chase for Dare is a certified 5K course with a Kids Fun Run and virtual option. It is a full day of family fun followed by a night of festivities and fireworks at night. All proceeds benefit the Town of Easton Drug Abuse Resistance Education (D.A.R.E.) program, which is run and maintained solely on donations. 

September 18 {Norwalk}

The Lighthouse Run for Greens Ledge Light has an in-person sunset 5K run, a 1-mile walk, and a virtual option. It is hosted at Bayley Beach in Rowayton, and all proceeds go to benefit the Greens Ledge Lighthouse.

September 19 {Darien}

The Darien Road Race will take place at Pear Tree Point Beach and hosts a 5-mile run and a 1.5-mile fun run. The race will feature “The Finish Line” tent with music, games, sponsor booths, raffle items, and an awards ceremony. Proceeds will benefit a host of community initiatives, including the Thriving Youth Task Force, The Human Services Planning Council, and the Touch-a-Life Program.

September 25 {Newtown}

The third annual Run 4 Hunger and Health is hosted by the Newtown Knights of Columbus and will be benefitting the Faith Food Pantry and Newtown Youth and Family Services. There will be a 5K walk/run race and a kid’s event directly following the conclusion of the main event.

September 26 {Southport}

The Bigelow Tea Community Challenge 5K run, 3K walk, and Kids Fun Run will take place rain or shine at the Wakeman Boys and Girls Club in Southport. Proceeds go to benefit 25 local charities.

September 26 {Stamford}

Miles for a Mission will host a virtual and in-person 5K option at St Francis Episcopal Church in Stamford. Canines are welcome at the in-person run/walk race. All proceeds benefit Person to Person, a Fairfield County charity organization providing food, clothing, and household necessities to local homes.

October 3 {Norwalk}

The Sono Half Marathon hosts a half marathon, a 5k, and Kids Fun Run at Veteran’s Park. There will be Finisher’s medal for all 1/2 marathon and 5K finishers. Finisher’s medallions for all Kid’s Fun Run participants will be available as well. 

October 3 {Wilton}

Where the Wild Things Run at Woodcock Nature Center will have a 5K trail and Kids Fun Run to benefit the Woodcock Nature Center’s educational programs. The race welcomes runners, walkers, and hikers of all ages. The Kid’s Fun Run is geared towards children 6 and up.

October 16 {Bridgeport}

The fifth annual CES 5K Fall Classic is to be held at beautiful Seaside Park in Bridgeport. Proceeds go to benefit the schools and programs of the Cooperative Educational Services.

October 17 {Trumbull}

The 2021 Great Pumpkin Classic will have a 5K run, 1-mile Health Walk, and Kids Fun Run. All proceeds will go to benefit Trumbull High School Scholarship Program and the Trumbull Chamber of Commerce.

October 17 {Ridgefield}

The Pamby Ridgefield Half Marathon and 7-miler is a beginner-friendly course covering some of the prettiest roads in Fairfield County. Proceeds go to benefit the Boys and Girls Club of Ridgefield.

October 24 {Weston}

The Reservoir Run offers a half marathon, 5K, and Kids Fun Run. The race begins and ends at Weston High School. Proceeds go to benefit the Kiwanis Club of Weston Foundation, Inc. (501(c)3) for The Connecticut Food Bank FOODSHARES programs and The Child & Family Guidance Center (CFGC) programs. The 5K proceeds will go to the Weston Boosters Club for the leaders training programs.  

October 31 {Redding}

Redding Road Race, A Run for the Cows, is hosted at New Pond Farm in West Redding with a half marathon, 7-mile run, and a Kids Fun Run. Extra perks include a large food spread, massage therapy, and a yoga class to help relax the muscles at the end of the race.

November 7 {Darien}

Run with the Saints at Saint Luke’s Parish will have a 5K run and a 1 mile Kids Fun Run/adult walk. The race starts and finishes at St. Luke’s Church. All walkers and kids under 10 should do the 1-mile walk. Proceeds go to the church, and lunch will follow the race for all participants.

 November 21 {Danbury}

The Tarrywile Half Marathon will be hosted at Tarrywile Park and is a tough half marathon trail course. Post-race celebration to follow with pre-packaged snacks and live music (state guideline permitting).

Are you planning to do any of these races this fall? Did we miss any of your favorites?


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