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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay

Saturday October 25, 2025 Ives Farm, 1585 Cheshire St. Cheshire, CT 06410

Event Description

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

Countdown to the 2025 Cheshire Community YMCA Harvest Trail Race

Events

5K Trail Race

$38.10 incl. $3.10 Fee 10/25 10:00AM EDT Registration ends October 24, 2025 at 11:59pm EDT

Y Cup Relay

$16.90 incl. $1.90 Fee 10/25 10:05AM EDT Registration ends October 23, 2025 at 11:59pm EDT

Pumpkin Dash

$0 10/25 9:45AM EDT Registration ends October 24, 2025 at 11:59pm EDT

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

$0 09/24 5:30PM EDT - 6:30PM EDT Registration ends September 22, 2025 at 11:59pm EDT

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

$0 10/01 5:30PM EDT - 6:30PM EDT Registration ends October 1, 2025 at 11:59am EDT

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

$0 10/08 5:30PM EDT - 6:30PM EDT Registration ends October 8, 2025 at 11:59am EDT

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

$0 10/15 - 10/20 5:30PM EDT - 6:30PM EDT Registration ends October 15, 2025 at 11:59am EDT

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

$0 10/22 5:30PM EDT - 6:30PM EDT Registration ends October 22, 2025 at 11:59am EDT
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Race Map

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