Cupid Made Me Do It 2 Mile Urban Challenge

This 2 mile road race starts and ends on Riverside Dr in Willimantic and runs through downtown, crossing three bridges.

T-SHIRTS guaranteed if registered by midnight, Feb 1st, 2026 (must be present at event to receive)

Registration $30 through February 6th, 2026   $10 Age 6 to 12    Age 5 and under FREE           $35 Race Day/ $20 Age 12 and Under    

TEAMS: Create a team or join and existing team. Compete for Team Awards: Largest Team, Most Enthusiastic Team, Most Spirited Team, Most Cupid-like Team, Most Holiday Inspired Team (Costumes encouraged)  

INDIVIDUAL AWARDS: will be given to the overall Male, Female, and Non-Binary finishers plus top three in the following age groups: 5 and under, 6-12, 13-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70-79, 80+.

The overall Male, Female, and Non-Binary winners as well as each age group winner will receive a gourmet cupcake donated by A CUPCAKE FOR LATER.

Race day registration starts at 8:30 at the First Baptist Church and the race starts at 10:00. A portion of the proceeds go to the Windham Area Interfaith Ministry.

This race is part of the schedule of events for the Romantic Willimantic Chocolate Festival.

This is event is being produced by FIRST MILE RACE MANAGEMENT.

Professionally chip timed by TK Timing.