Trail Running calendar near Chester 2025-2026

We have found 62 Trailruns within 80 miles of Chester. See below where and when you can find the races.

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..

May 2026

Breakneck Point Trail Runs, hosted by Red Newt Racing, take place at University Settlement Camp in Beacon, New York. The event offers two challenging distances: a half marathon of 14.5 miles with approximately 4,800 feet of elevation gain, and a full marathon of 26.4 miles with about 9,000 feet of g..