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 the Cheshire Land Trust are presenting a community running event around historic Ives Farm. The course winds through fields and trails on the property, with the start and finish located at the restored barn. Proceeds will support YMCA programs in the Cheshire community and the Cheshire Land Trust’s revitalization plans for Ives Farm.
Distances offered:
- 5K Trail Race - varied terrain and slight elevation
- Y Cup Relay - teams of three elementary students, each runs one mile
- Pumpkin Dash - free 400 meter race for children six and under
The 5K Trail Race is described as beginner friendly and includes varied footing and some slight climbs, making it an option for road runners trying a trail and for experienced trail runners to work on speed. The Y Cup Relay involves teams from elementary grades competing for the Y Cup for the 25-26 school year and will be run in honor of a longtime local physical education teacher who supported the event. The Pumpkin Dash takes place on the dirt roads of Ives Farm and shares the main race finish line.
Family friendly activities will be available, including pumpkin decorating, face painting, Halloween mask making, games, live music, and a fall theme photo booth. Visit the organization's website for the most recent information.