Trail Running calendar near Cheshire 2025-2026

Tackle multi day ultras and relays at the Iron Hike Fall series in Cornwall CT, Oct 1 to 4, 2026. Presented by a veteran owned production team, events offer run, hike or walk options across epic mountain terrain.

Take on a 24 hour trail challenge at Mohawk Mountain with a 28 plus mile course and huge elevation gain that rewards grit and strategy. Run, hike, or walk solo or as a relay with veteran owned IronHike Endurance Productions.

Conquer Mohawk Mountain on scenic but rugged trail courses with 5K, 10K, half marathon and marathon options, big climbs and singletrack. Runners earn finisher medals, enjoy aid stations and follow a cupless policy to reduce waste.

Tackle a scenic half marathon loop through five parks in Westchester, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly wooded trails, rocky roots and abundant wildlife make this a classic trail escape.

Test your legs on rugged singletrack at Harriman State Park with Big Bear SquaTCh South, a half marathon or 10K on Oct 18, 2026 that supports trail maintenance. Limited to 175 runners, this sold out favorite features steep climbs rocky root..

Enjoy a scenic 5 mile trail run through historic Muscoot Farm in Katonah, with fun kids races and farm market perks. Finishers get Farm Bucks to spend at the market, making this a perfect fall family run and local food celebration.

Run or walk the family friendly Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on November 14, 2026. Enjoy post race refreshments and a festive community atmosphere.

Run 13.1 miles on forest trails at the Storybook Half Marathon in Roosevelt Forest, Stratford CT, completing eight scenic loops of single and doubletrack. Wear a costume, enjoy post race perks, and donate children's books to Books4Everyone.