Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
Cheshire Community YMCA Harvest Trail Race and Y Cup Relay is a running and trail running race on September 16 – October 24, 2026 in Cheshire, CT, with entry fees from $17 to $38.
- Date
- September 16 – October 24, 2026 (Race day is today)
- Location
- 1585 Cheshire St., Cheshire, CT
- Price
- $17–$38
- Sports
- RunningTrail Running
From the Organizer
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
Events
Race-Day Forecast
Live forecast from the U.S. National Weather Service.
Race Day 1
Wednesday, 9/16
High
77°
Low
59°
Mostly sunny
Race Day 2
Thursday, 9/17
High
80°
Low
64°
Patchy fog then partly sunny
Race Day 3
Friday, 9/18
High
78°
Low
49°
Mostly sunny
Race Day 4
Saturday, 9/19
High
68°
Low
50°
Mostly sunny
Race Day 5
Sunday, 9/20
High
67°
Low
52°
Rain showers likely
Race Day 6
Monday, 9/21
High
69°
Low
52°
Chance rain showers
Race Day 7
Tuesday, 9/22
High
70°
Low
—
Chance rain showers
About Cheshire, CT
City Elevation
133 ft
Nearest Airport
HVN
Tweed New Haven Airport · 13 mi
Major Hub
BDL
Bradley International Airport · 35 mi
Time Zone
Eastern Time
From Endurance Grid
Line up lodging and travel early to lock in your race weekend.
Race Location
What Are You
Waiting For?
Every finish line starts with a single decision. Claim your spot at Cheshire Community YMCA Harvest Trail Race and Y Cup Relay, put it on the calendar, and turn “someday” into a start date.
Today
Race day is here
- Race
- Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
- Date
- September 16 – October 24, 2026
- Location
- 1585 Cheshire St., Cheshire, CT
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About These Sports
This race spans more than one sport — here’s a guide to each, so you can understand what’s involved and decide if it’s the right fit. For course distances, logistics, and race-day specifics, always defer to the race organizer’s event page.
Running
From 5K to marathon, running races are an accessible entry point into endurance sport. There's a distance for every fitness level and a community at every start line.
Trail Running
Running off-road — dirt, singletrack, and mountain paths — from 5Ks to ultras. The terrain makes for an exciting twist and adventure in your running journey.
More Running races near Cheshire, CT
Frequently Asked Questions
What is the Cheshire Community YMCA Harvest Trail Race and Y Cup Relay?
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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay
Sep 16, 2026