Cupid Made Me Do It

Embrace the spirit of Valentine's weekend with the Cupid Made Me Do It 2 Mile Urban Challenge, set to take place on Saturday, February 7, 2026, in scenic Willimantic, CT. This delightful 2-mile road race offers a charming journey through the heart of downtown, starting and finishing on Riverside Drive, and features crossings over three picturesque bridges. Expect typical race day conditions with highs around 37°F and lows near 18°F, accompanied by a low 12% chance of precipitation, making for invigorating winter running.

This event is more than just a race; it's an integral part of the Romantic Willimantic Chocolate Festival, promising a lively community atmosphere. Runners are encouraged to get into the holiday spirit by donning Cupid-inspired or festive costumes, competing for unique team awards such as Largest, Most Enthusiastic, and Most Spirited Team. Individual category winners receive a delicious gourmet cupcake, adding a sweet reward to your accomplishment. Race day registration kicks off at 8:30 AM at the First Baptist Church, with the race officially starting at 10:00 AM. A portion of the proceeds from this festive run will benefit the Windham Area Interfaith Ministry, allowing you to run for a good cause.