Trail Running Calendar New York 2026-2027

Turkey Trot 2026 in Ithaca is a roughly 5.5-mile prediction run with no watches allowed, supporting Loaves and Fishes. Participants predict their time and the closest guesses win pies.

The NSRF Leftover Turkey Trot 5K will take place in Bethpage on Saturday 28 November 2026. You can run 5 kilometers.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

The NSRF 50/50 Turkey Trot 5K will take place in West Babylon on Sunday 29 November 2026. You can run 5 kilometers.

A looped ultramarathon in Prospect Park, Brooklyn offering 50 mile and 50 kilometer options. The course uses 3.33 mile loops and includes on course hydration and a potluck style aid station.

A winter trail festival at Powder Mills Park offering 5, 10, and 15 mile options on a looped single-track course, green-race refill-only hydration, limited registration, and a custom hot cocoa mug for early registrants.

Frozen Assets Endurance Run is a 10k endurance event at Harriet Hollister Spencer SRA on January 2, 2027. The listing shows a single 10k race distance at that location.

Experience a winter trail race at Ontario County Park with options for one, two, or three 4 mile loops. Enjoy a heated lodge and hot pancakes after navigating the seasonal snow and ice of the Bristol Hills.

The Stone Wall is listed as the Orange Course at Winona Forest with a January 19, 2025 date but is marked as not taking place in 2025; the venue has more than 50 miles of groomed, wooded trails and heavy annual lake effect snow.

A late winter trail race at Gilbert Lake State Park on February 21, 2026 offering 50k, 25k, and 10k on a 6+ mile loop with a snow adjusted course and an aid station serving hot broth and snacks. Net proceeds support The Neighborhood Center.

A winter road race on February 27, 2027 in Cape Vincent, NY, offering 10k, half and full marathon options along a flat out-and-back to Tibbetts Point Lighthouse. Hot showers, aid stations, and postrace refreshments are provided.

The NSRF 4-Leaf Clover 5K Trail will take place in Old Bethpage on Sunday 28 March 2027. You can run 5 kilometers.

The NSRF The Bunny Trail 5K will take place in Bethpage on Saturday 3 April 2027. You can run 5 kilometers.

The Big Bear Squatch North will take place in Woodbury on Saturday 3 April 2027. You can run between 10 and 13 miles.

The Run for the Rescue 5K Trail Run/Walk will take place in Hauppauge on Saturday 10 April 2027. You can run 5 kilometers.

A trail race at Green Lakes State Park offering 10 mile, 20 mile, and 50 km options on a roughly 10.4 mile loop with varied surfaces, two aid stations, and on course food plus postrace ramen and vegan options.

The Squatchywaska Mountainfest will take place in Ellenville on Saturday 24 April 2027. You can run between 10 and 17 miles.

Squatchywaska Mountainfest in the Shawangunk Ridge on April 24, 2027 features a technical 25K and a 10 mile lollipop course with steep climbs, rocky singletrack, two aid stations, and a six hour cutoff.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.

The Denfit Ultra will take place in Cape Vincent on Sunday 9 May 2027. You can run between 50 and 100 kilometers.