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.

A community 5K in Batavia, NY on November 26, 2026 with 100% of proceeds to Crossroads House; family and stroller friendly, post-race refreshments, and a listed entry fee of USD 43.50.

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.

An ultramarathon in Prospect Park, Brooklyn on December 6, 2026 offering 50K and 50 mile looped courses with potluck-style aid, Skratch Labs hydration, chip timing, and finisher belt buckles.

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.

A weekend trail event in Blydenburgh County Park featuring a Backyard Ultra with 4.167 mile hourly loops and a separate 4.16 mile lapping race. A portion of proceeds supports the Long Island Greenbelt Trail Conference.

A winter trail race in Harriet Hollister Spencer State Recreation Area near Springwater, NY. The course is an approximately 10k loop on single track trails, likely snowy, with no aid stations and snowshoes not permitted.

A winter trail event in Ontario County Park on January 16, 2027 with 4, 8 and 12 mile options run as one to three laps of a 4 mile loop. The day includes a heated lodge, pancakes, winter demos, and relaxed registration policies.

A winter trail event at Mendon Ponds Park offering 50k, 25k and a rebranded 5 mile with post-race ice cream. Hopkins Point Lodge serves as race HQ and aid station with hot drinks and food as runners complete loops.

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.

Chip timed 5k run and walk at Osprey’s Dominion Vineyards in Peconic, NY on March 20, 2027, over a two lap cross country loop with a postrace wine pour for eligible participants. Registration includes a T shirt, collapsible wine glass and f..

A chip-timed 5K run and walk at Three Brothers Wineries & Estates in Geneva, New York on March 27, 2027, with race swag, a cider donut and a pour of cider included; results are posted online.

A 5K trail run at Bethpage State Park with a free kiddie fun run and a virtual option, a good luck shirt, on course hydration, post race refreshments, and age group recognition. Beer is available for participants 21 and older with ID.

A 5K trail run and a free kiddie run at Bethpage State Park with in-person and virtual options, onsite refreshments, mailed bibs, and online results. Donations support the Never Stop Running Foundation.

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY, on mixed terrain with dog friendly policies. Event proceeds support Last Chance Animal Rescue and online recognition is given for top age group finishers.

A trail race at Green Lakes State Park near Fayetteville, NY with 50 km, 20 mile, and 10 mile options on a ~10 mile loop featuring varied terrain, two aid stations, and postrace ramen with vegan options.

Two mountain trail races in the Shawangunk Ridge on April 24, 2027. The technical 25K and 10 mile routes feature cliffs, steep climbs, two aid stations, strong course markings, and a 150 participant cap.

A mountain trail festival near Ellenville NY offering a technical 25K (about 17 miles) and a 10 mile course, both limited to 150 entrants with a six hour cutoff. The routes feature steep climbs, rocky singletrack, and two stocked aid statio..