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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Saturday October 25, 2025 Ives Farm
Cheshire, CT 06410 US

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. 
Event Date:
Saturday October 25, 2025
Start Time:
10:00am EDT
Price:
$38.10 incl. $3.10 Fee
Registration:
Registration ends October 24, 2025 at 11:59pm EDT

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.
Event Date:
Saturday October 25, 2025
Start Time:
10:05am EDT
Price:
$16.90 incl. $1.90 Fee
Registration:
Registration ends October 23, 2025 at 11:59pm EDT

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.
Event Date:
Saturday October 25, 2025
Start Time:
9:45am EDT

Y Cup 5-Week Practice Series - 9/24/2025

Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at briollano@sccymca.org or 203-272-3150x511 with questions.
Event Date:
Wednesday September 24, 2025
Start Time:
5:30pm EDT
End Time:
6:30pm EDT

Y Cup 5-Week Practice Series - 10/01/2025

Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at briollano@sccymca.org or 203-272-3150x511 with questions.
Event Date:
Wednesday October 1, 2025
Start Time:
5:30pm EDT
End Time:
6:30pm EDT

Y Cup 5-Week Practice Series - 10/08/2025

Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at briollano@sccymca.org or 203-272-3150x511 with questions.
Event Date:
Wednesday October 8, 2025
Start Time:
5:30pm EDT
End Time:
6:30pm EDT

Y Cup 5-Week Practice Series - 10/15/2025

Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at briollano@sccymca.org or 203-272-3150x511 with questions.
Event Dates:
Wednesday October 15, 2025 - Monday October 20, 2025
Start Time:
5:30pm EDT
End Time:
6:30pm EDT

Y Cup 5-Week Practice Series - 10/22/2025

Join us for a special 5-week practice series designed for our young athletes participating in the Y-Cup! This program meets Wednesdays from 5:30-6:30 Sept. 24-Oct 22 at our new YMCA location (435 North Brooksvale Rd. Cheshire). Each practice will focus on building endurance, improving speed, and developing proper running mechanics. Our goal is to help participants gain confidence, strengthen their performance, and prepare for race day on the Harvest Trail. Contact Brandon Riollano at briollano@sccymca.org or 203-272-3150x511 with questions.
Event Date:
Wednesday October 22, 2025
Start Time:
5:30pm EDT
End Time:
6:30pm EDT

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