Trail Running calendar near Cheshire 2025-2026

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.

Run the scenic Shawangunk Ridge in Rosendale NY with 70 mile, 30 mile and half marathon trail options through cliffs, lakes and pine barrens. Minimally supported and self supported, the event is a true test of endurance and trail skill.

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.

Wawayanda State Park in Hewitt NJ hosts a trail festival on September 19 and 20, 2026 with races from a kids mile to a 100 mile challenge, evening panels and free camping. Join a welcoming community supporting Bigger Than The Trail.

Hit the newly restored Moosup Valley State Park Trail on Sunday, September 27 for scenic 5K, 10K and a kids fun run on all trail terrain. Post race food and gear, leashed dogs welcome, and proceeds support the Rotary Club of Plainfield.

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.