Race Report: Cheshire Community YMCA 5K Harvest Trail Race

Today, I'll be recapping the Cheshire Community YMCA 5K Harvest Trail Race at Ives Farm. This event included a kids run called The Pumpkin Dash, a 1.5km walk, a trail 5k, and a relay version of the trail 5k for kids called the Y Cup Relay.

Date: October 24, 2026

Town: Cheshire, CT, USA

Distance: 5k (course was slightly short)

Conditions: It was a chilly but very sunny day for the 2026 event. It was 43°F (6°C) when the race started at noon. It was a little breezy.

Parking: There was limited parking at Ives Farm itself, then more parking in a field across the street. There were police officers directing traffic and marshals to direct parking throughout the field. I did notice parking was running out when I arrived 35 minutes before the race start but the marshals were confident they would find an overflow parking area to use.

Check In: There was no line at check-in, which was in a small tent by the big red barn. I received a cute knit hat at check-in, which I immediately donned because it was freezing.

Course Description: This was a challenging trail course, but it was very well-marked. Tree roots and rocks were spray-painted in white and the turns were marshalled by volunteers.

The course starts at Ives Farm by the barn, and immediately heads downhill across the road into the parking field. Then, the course takes a brutal uphill on grass and then onto a trail entering the woods. The first mile definitely had the most hills, and it was my slowest mile for sure. At the end of that first mile, there was a water stop and a relay exchange for the kids race.

The second mile included a wooden bridge crossing and more hills in the woods. The trail exited the woods just after the second mile marker, where there was another relay exchange and water stop.

The third mile involved crossing the road again (police stopped traffic) and then doing a big loop around an agricultural field. The final push was up a small rise to the start/finish line by the red barn.

Course Map

Afterparty: This was a cute race for families with young kids. There was a little pumpkin patch to take pictures and there was music playing. I saw some refreshments, including apples and bagels with cream cheese, but I generally avoid taking any food that children are allowed to freely handle like that. 

Notably, there was a large sign indicating there was coffee, hot apple cider, and apple cider doughnuts in the red barn. I entered to find it nearly empty, because there was a table selling said items. Personally, I assumed those would have been included in the cost of the race.

Knit hat