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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Saturday October 24, 2026
Ives Farm
Cheshire, CT 06410 US

5K Trail Race

This is a 5k trail race with varied terrain and slight elevation which winds through groomed wooded paths and open fields - 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 24, 2026
Start Time:
10:00am EDT
Price:
$41.28 incl. $3.28 Fee
Registration:
Registration ends October 24, 2026 at 9:55am EDT
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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 26-27 school year.
Event Date:
Saturday October 24, 2026
Start Time:
10:05am EDT
Price:
$19.02 incl. $2.02 Fee
Registration:
Registration ends October 24, 2026 at 11:59pm EDT
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Pumpkin Dash

A free race for children 6yr and younger on the dirt path around the historic Ives Farm barn. Young runners will end the dash by running through the same race finish line as all other racers!
Event Date:
Saturday October 24, 2026
Start Time:
9:45am EDT
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Y Cup Relay - FREE 6 Week Training Series (1/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday September 16, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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Y Cup Relay - FREE 6 Week Training Series (2/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday September 23, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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Y Cup Relay -FREE 6 Week Training Series (3/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday September 30, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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Y Cup Relay - FREE 6 Week Training Series (4/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday October 7, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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Y Cup Relay - FREE 6 Week Training Series (5/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday October 14, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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Y Cup Relay - FREE 6 Week Training Series (6/6)

This is a FREE 6-week training session for elementary-aged students. All sessions conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Date:
Wednesday October 21, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
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5K FREE - 6 Week Training Series Dates 9/16, 9/23, 9/30, 10/7, 10/14, 10/21

This is a FREE 6-week training series for runners looking to prepare for the 5K Harvest Trail Race, improve their fitness, and train alongside others in a supportive environment.

All sessions will be conducted at:
435 North Brooksvale Rd.
Cheshire, CT 06410
Event Dates:
Wednesday September 16, 2026 - Wednesday October 21, 2026
Start Time:
5:30pm EDT
End Time:
6:30pm EDT
Price:
$0.00
Registration:
Registration ends October 21, 2026 at 5:00pm EDT
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