Tomorrow! · Wed, Sep 16, 2026
Don't let race day sneak up
One email during race week. That's it.
Wednesday, September 16th, 2026
1585 Cheshire St., Cheshire CT
5K
45–61°F · some rain risk
See last 10 years
On this date: rain 3 of the last 10 years
2025
41–57°F
dry
2024
51–67°F
dry
2023
39–60°F
dry
2022
51–59°F
rain
2021
41–59°F
dry
2020
47–67°F
dry
2019
43–64°F
dry
2018
39–51°F
dry
2017
64–70°F
rain
2016
46–58°F
rain
Best months to race in Connecticut →
Race-day forecast · Wednesday, Sep 16
Cloudy · 55–73°F
Wednesday, Sep 16starts near 55°F · 3% chance of rain · wind up to 7 mph
About this race
Event Overview
The Cheshire Community YMCA and Cheshire Land Trust are partnering on a race around historic Ives Farm. This all-ages run will wind through the fields and trails on the property, with the start and finish line located at the beautifully restored barn. Proceeds from this event will support the work that the YMCA does in the Cheshire community as well as the revitalization plans that the Cheshire Land Trust has for the Ives Farm property.
Activities
- Kids' Event: Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
- Family Fun: Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth.
Race Schedule
- Pumpkin Dash Start: 9:45AM
- 5K Start: 10:00AM
- Y Cup Relay Start: 10:05AM
Location
1585 Cheshire St., Cheshire, CT.
More Information
For more details, visit the race page: Cheshire Community YMCA Harvest Trail Race and Y Cup Relay.
Course map
Hotels for race weekend
Live prices near the start line, Sep 15 – 17, 2026.
Train with a club
Run clubs near Cheshire to train with before race day.
Suggested Races
Organize this race?
Claim it free to manage your listing — and get it featured for free, while spots last.