Cheshire Community YMCA 5K Harvest Trail Run
Cheshire, United States • 24 Oct 2026
Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
The Cheshire Community YMCA and Cheshire Land Trust present a community running event at historic Ives Farm. The route winds through fields and trails on the property, with the start and finish located at the restored barn. Proceeds support YMCA programs in the Cheshire community and the Cheshire Land Trust's revitalization plans for Ives Farm.
The event program includes a trail 5K described as beginner friendly, with varied terrain and some slight elevation. The Y Cup Relay is a team event for elementary school students: teams of three each run one mile of the 5K course, and teams from all grades compete to determine which school wins the Y Cup for the 25-26 school year. A free Pumpkin Dash for children six and under takes place on the dirt roads of Ives Farm; those kids will run through the same finish line used by other races.
Family friendly activities are scheduled alongside the races and include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth.
Event distances: Visit the organization's website for the most recent information.
- 5K Trail Race 5 kilometers
- Y Cup Relay 5 kilometers team total
- Pumpkin Dash 400 meters