Cupid Made Me Do It 2 Mile Urban Challenge

Race Overview

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

T-Shirts

• Guarantee: T-Shirts guaranteed if registered by midnight, Feb 1st, 2026 (must be present at event to receive).

Registration Fees

• Standard Registration: $30 through February 6th, 2026.
• Children Ages 6 to 12: $10.
• Children Ages 5 and under: FREE.
• Race Day Registration: $35: $20 for Age 12 and Under.

Teams

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

Individual Awards

• Categories: Awards for 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+.
• Special Prize: Winners will receive a gourmet cupcake donated by A CUPCAKE FOR LATER.

Event Details

• Registration Start: Race day registration starts at 8:30 at the First Baptist Church.
• Race Start: The race starts at 10:00.
• Beneficiary: A portion of the proceeds will go to the Windham Area Interfaith Ministry.
• Festival Connection: This race is part of the schedule of events for the Romantic Willimantic Chocolate Festival.

Event Production

• Produced By: FIRST MILE RACE MANAGEMENT.
• Timing: Professionally chip timed by TK Timing.

Registration Link

For more information and to register, visit: Cupid Made Me Do It 2 Mile Urban Challenge.