Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Cheshire Community YMCA Harvest Trail Race and Y Cup Relay is held in Cheshire, Connecticut, on October 24, 2026, with three ways to take part. The quarter-mile Pumpkin Dash opens the morning at 9:45 a.m., the 5K trail race follows at 10:00 a.m., and the Y Cup Relay, also run on the 5K trail course, sets off at 10:05 a.m.

Trail running is slower than road running for the same effort, so judge this one by how hard you are working rather than by your usual 5K time, and wear shoes that grip. The relay format is a good introduction for anyone nervous about racing alone, since each runner covers only part of the course with teammates waiting. The tight schedule also makes it easy for a family to spread across the Pumpkin Dash and the 5K and be done within the hour.