Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT

Date
October 24, 2026
Location
Cheshire, CT
Venue
1585 Cheshire St.
Start Time
9:45 AM
Entry Fee
$0.00 – $38.00
Events
5K Trail Race, Y Cup Relay, Pumpkin Dash
Includes
Custom Harvest Trail Race Hat | Finisher Medal
Register NowRegistration Open

The Cheshire Community YMCA Harvest Trail Race and Y Cup Relay costs between free and $38 to enter, making it an accessible option for runners of all budgets. Taking place on October 24, 2026, at 1585 Cheshire Street in Cheshire, Connecticut, the event starts at 9:45 AM and offers both trail running and road running formats. Participants can choose from a 400-meter option or a 5K distance, with relay teams also welcome. Whether you're looking for a short speed effort or a longer trail outing, this YMCA-hosted event provides flexible racing options for the local running community.

From the Race 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

Hotels Near This Race

Find accommodation close to the start line in Cheshire, CT. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT

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Race Travel Insurance

Don't forget travel insurance for October 24.

You've trained for months and booked a trip to Cheshire, CT. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

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Frequently Asked Questions

When is Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT?

Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT takes place on October 24, 2026. The race is held in Cheshire, Connecticut.

Where is Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT held?

Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT is held at 1585 Cheshire St. in Cheshire, Connecticut.

Where can I find hotels near Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026 — Cheshire, CT?

RaceHotelFinder shows hotels sorted by distance from the race venue in Cheshire. Use the map or list view on this page to compare options and book race weekend accommodation.