Trail Running calendar near Cheshire 2025-2026
We have found 68 Trailruns within 80 miles of Cheshire. See below where and when you can find the races.
We have found 68 Trailruns within 80 miles of Cheshire. See below where and when you can find the races.
Hit the fields at Waters Farm on Sunday, August 23, 2026 for the Old Goat Track Club XC Classic, a fast and friendly 5K cross country through scenic farm trails. A USATF New England Grand Prix stop with race day registration available.
Tackle a scenic 5K through Oswegatchie Hills Nature Preserve, winding past Clark Pond on root and rock strewn trails; hikers welcome. This fourth annual run benefits preserve maintenance and finishes with local pub awards and camaraderie.
Push your limits at the Pawling 24 Hour Trail Festival in Lakeside Park Sept 19 to 20 with timed 3 to 24 hour loop races day or night. Enjoy a scenic loop, food, music and a welcoming runner community.
Take on the Iron Hike Fall Olympus Mons Ultra Trail Marathon Relay in Cornwall Connecticut, a team endurance challenge across Mohawk Mountain covering 152 plus miles with massive elevation gain. Run, hike or walk the course within an 84 hou..
Run a scenic 13.1 mile trail half in Roosevelt Forest with eight laps on a marked loop, aid on every lap, awards and costume prizes, plus a book drive for local kids. All get a medallion and Athletic Brewing non alcoholic beer.