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Cheshire Community Ymca Harvest Trail Race and Y Cup Relay
Cheshire Community Ymca Harvest Trail Race and Y Cup Relay logo

Cheshire Community Ymca Harvest Trail Race and Y Cup Relay

Cheshire, Connecticut, United States
Oct 24, 2026
Running

About the Event

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

Join fellow runners on October 24, 2026 for the Cheshire Community Ymca Harvest Trail Race and Y Cup Relay. It's a fantastic 5K, Pumpkin Dash featuring a flat and fast course in Cheshire.

Races Offered

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. 

Oct 24, 2026 5K 10:00
$38.00
Open

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.

Oct 24, 2026 5K 10:05
$17.00
Open

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.

Oct 24, 2026 Pumpkin Dash 09:45
Free
Open

About Cheshire

Cheshire Community Ymca Harvest Trail Race and Y Cup Relay takes place in Cheshire, Connecticut, United States. The local timezone is America/New_York.

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Race information has been sourced from the event's official website and other publicly available resources. For the most up-to-date details, please refer to the official website directly. If you notice any incorrect or missing information, don't hesitate to reach out to us by email.

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