Trail Running Calendar New York 2025-2026

The Cat's Tail Marathon will take place in Shandaken on Saturday 26 September 2026. You can run 26 miles.

Join the Live Well Community Wellness 5K on Sunday, Sept 27, 2026 for a scenic forest run along the Greenway Trail in Dolgeville, NY. Proceeds provide free sports equipment to local youth and early registrants receive a free race tee.

Amy's Adventure Race for the Lake features scenic 4.5 mile and 10 mile trail courses through Amy's Park with ponds, marshes and about 700 feet of climbing. Proceeds benefit Lake George Land Conservancy and virtual entries are welcome.

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.

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.