Cheshire Community YMCA Harvest Trail Race and Y Cup Relay 2026
- Date
- Saturday, October 24, 2026
- Start time
- 9:45 AM start (New York)
- Location
- Cheshire, Connecticut
- Entry fee
- From Free
- Included with entry
- Includes a finisher medal and a hat
- Fundraising
- Takes optional donations when you register
Registration is open.
We earn a small commission when you register through this link, at no cost to you. Details
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Events and entry fees
| Event | Distance | When | Entry fee | Cap |
|---|---|---|---|---|
| Pumpkin Dash | Other | Oct 24, 20269:45 AM | Free | – |
| Fit N Fun Adaptive 1.5K Run | 1 Mile | Oct 24, 20269:55 AM | $17 | – |
| 5K Trail Race | 5K | Oct 24, 202610:00 AM | $38 | – |
| Y Cup Relay | Relay | Oct 24, 202610:05 AM | $17 | – |
Entry fees exclude processing fees. Prices and dates come from the race's registration page and refresh nightly.
Race day planning
Entry fee schedule
- Pumpkin Dash: Free until Oct 23.
- Fit N Fun Adaptive 1.5K Run: $17 until Oct 23.
- 5K Trail Race: $38 until Oct 24.
- Y Cup Relay: $17 until Oct 24.
Online registration closes Oct 24, 2026, unless the race fills first.
How the price compares
At $38, entry is about 12 percent above a typical 5K in Connecticut, which costs $34 right now.
What a typical finish looks like
A typical finisher at a 5K in Connecticut runs 37:07, about 11:57 a mile, based on 10 races with published results. Women typically finish in 39:29 and men in 33:44.
Light and altitude
Sunrise on race morning is at about 7:12 AM, and the Pumpkin Dash starts at 9:45 AM. The start sits about 240 feet above sea level.
Fees exclude processing fees. Comparisons use current entry fees and published results from races nearby.
Start location and course
1585 Cheshire St., Cheshire, CT 06410
The pin marks the address the race lists, which is usually the start. The organizers have not shared a course map with us yet.
2025 results
All resultsAggregated from official results (Startline Race Services) for Cheshire Community YMCA Harvest Trail Race and Y Cup Relay. Individual finisher names are not stored here.
How fast do you need to be at Cheshire Community YMCA Harvest Trail Race and Y Cup Relay?
In 2025, the fastest tenth finished in 26:00 or better, the top quarter in 28:14, and half the field in 31:28; the last tenth came in after 46:29.
| Age | Women | Men |
|---|---|---|
| Under 20 | 27:57 | 27:01 |
| 20-29 | 31:50 | n/a |
| 30-39 | 30:13 | 25:53 |
| 40-49 | 28:23 | 27:49 |
| 50-59 | n/a | 28:22 |
Groups with fewer than five finishers are left out. Awards vary by race; check the race's rules.
What would my time get me?
Where a finish time would have placed in 2025.
How fast is it?
Faster than most Connecticut trail 5Ks
The fastest quarter of the 2025 5K field finished under 28:14, against 29:17 in a typical Connecticut trail 5K, so times here run 4 percent faster.
Compares the fastest quarter of each field, so walkers and first-timers do not skew it. It reflects the course and the field together: a flat course, cool weather, or a competitive crowd all make times faster.
Typical race-day weather
Around October 24 the day usually runs from 44°F at dawn to 60°F in the afternoon, with measurable rain on about 25% of days. Cold snaps dip to 37°F and hot years reach 72°F.
Based on 75 days within a week of the date over the last 5 years, from historical weather for the start area. Not a forecast.
Race details
- Where
- 1585 Cheshire St., Cheshire, CT 06410Map
- Course
- Trail
- Start elevation
- About 240 feet
- Included with entry
- Finisher Medal; Custom Harvest Trail Race Hat
- Donations
- Accepted when you register
- Distances
- 1 Mile, 5K, Relay, Other
- Editions
- 2026 (Sep 16, 2026), 2025 (Sep 24, 2025)
Organize this race? Add details or a correction
Plan your race
Quick answers
- When is Cheshire Community YMCA Harvest Trail Race and Y Cup Relay?
- Saturday, October 24, 2026, starting at 9:45 AM.
- How much does it cost?
- Entry starts at Free before processing fees.
- When does registration close?
- Online registration closes Oct 24, 2026, unless the race fills first.
- Is the entry fee high for Connecticut?
- At $38, entry is about 12 percent above a typical 5K in Connecticut, which costs $34 right now.
- Do runners get a shirt or medal?
- Entry includes a finisher medal and a hat, according to the race's registration page. Check it for sizes and whether kids' races get the same.
- Can I donate to a cause when I register?
- Yes. The registration form offers an optional donation, usually for the charity or nonprofit the race supports. The race's own page names the cause.
- What distances can I run?
- 1 Mile, 5K, Relay, Other.
- How big is it, and how fast?
- In 2025, 104 runners finished the 5K Trail Race; the median finish was 31:28 and the winner ran 19:54.
- Is it a fast course?
- The fastest quarter of the 2025 5K field finished under 28:14, against 29:17 in a typical Connecticut trail 5K, so times here run 4 percent faster.
- Where does it start?
- 1585 Cheshire St., Cheshire, CT 06410.
From the organizers
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