Cheshire Community Ymca Harvest Trail Race and Y Cup Relay
About this race
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.
- Prior to the race there will be a FREE Pumpkin Dash for kids 6 years old and younger.
- Family friendly activities include pumpkin decorating, face painting, Halloween mask making, games, live music and a fall theme photo booth
Pumpkin Dash Start: 9:45AM
5K Start: 10:00AM
Y Cup Relay Start: 10:05AM
Pick your distance
Trail running
5K Trail Race
This trail 5k is a great beginner friendly race with varied terrain and some slight elevation - perfect for the road runner wanting to try a trail run. It's also a good opportunity for an experienced trail runner to do some speed work.
Running
Y Cup Relay
Teams of 3 elementary school students will each run one mile of the 5K course. Teams from all grades will compete for their team to determine which school wins the prestigious Y Cup for the 25-26 school year. This year’s Y Cup Relay will be run in honor of Coach Jerry Webb who was a beloved Physical Education teacher at Highland School and an active part of the Y Cup Relay since it began. His support and enthusiasm for this event was contagious and resulted in a great turn out of young runners.
Pumpkin Dash
A free race for kids 6 and under on the dirt roads of Ives Farm. Kids will get a chance to run through the same race finish line as all other racers.
Typical race-day weather
Based on 2 years of historical conditions on this event's race dates in Cheshire.
Course
Route map and elevation profile
No course map published yet.
The organizer hasn't released a route for this event, and we don't publish guesses. If you're the organizer, send us a GPX file and we'll draw the profile.
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Other races near Cheshire
Different organizers, within 40 miles, in the next three months
Chamber Challenge 5K
Robert J. Lynes Memorial Road Race
Hot Coco 5K
Run The Runway 5K & Kids Fun Run
🏃 Plan Your Next Race in Cheshire
Find upcoming events by distance:
- Cheshire 5K Races 3 races
- Cheshire Running Calendar 2026 3 races
Where this page comes from. Race details were last updated on . We re-check listings regularly and again in the week before race day.
- Entries, prices, waves and inclusions — the event's official registration page
- Temperature and humidity — Copernicus ERA5 reanalysis via Open-Meteo (CC BY 4.0)
- Elevation and terrain relief — Copernicus DEM GLO-90, ESA (CC BY 4.0)
- Comparisons and counts — Race Discovery calendar, 3 Cheshire events
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