New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 149 exciting trail runs across the region. Find your next trail run in New York below and join the trail community at these great events!
November 2026
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
A Thanksgiving morning 5K and one mile fun run on Cazenovia Gorge Trail with chip timing, prizes, and a food collection.
A 5K run in Mayville, NY on 11/26/2026 with hills and lakefront sections along Chautauqua Lake, organized by the not for profit Inspire Good of WNY, INC.
A trail 5K run and walk at Bethpage State Park on Nov 28, 2026 with a virtual option, a free kiddie dash, event shirts, and postfinish refreshments.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
A trail 5K at Belmont Lake State Park in late November 2026 featuring a 50/50 raffle where half the net proceeds are awarded to present participants.
December 2026
A looped ultramarathon in Prospect Park offering 50K and 50 mile options, one aid station with Skratch hydration, chip timing, a 15 hour cutoff, and finisher 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 backyard ultra at Blydenburgh County Park: runners repeat a 4.167 mile loop each hour until one completes the final loop; proceeds support Long Island trail maintenance.
A 5K race at Van Cortlandt Park on December 12, 2026, with tiered registration pricing, bib pickup at the Tortoise and Hare Statue, T shirts and bag check.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
January 2027
Winter trail run at Harriet Hollister Spencer State Recreation Area on January 9, 2027, an approximately 10k loop and the first race of the Common Ground Winter Trail Series.
Winter trail race at Ontario County Park with one to three 4 mile loops, an added snowshoe option, and post-race pancakes and warm drinks.
Stone Wall is a January snowshoe event in Mannsville, NY with mass-start 5K and 10K races on wooded, variable winter trails; snowshoes required and loaners limited.
February 2027
Winter trail races at Mendon Ponds Park with 5 mile, 25k and 50k options and a lodge aid station serving hot drinks and food.
A winter road race in Cape Vincent along the St. Lawrence offering 10k, half and full marathon courses, hot showers, aid stations, medals and limited fields.
March 2027
Trail events at Sunken Meadow State Park on a roughly 1.4 mile loop with one hour and three hour formats awarding titles for greatest distance covered.
A chip timed 5K at Osprey's Dominion Vineyards in Peconic, NY on March 20, 2027. Entry includes a t-shirt, collapsible wine glass, finisher medal, chip timed bib and a pour of wine.
A chip timed 5K run and walk at Three Brothers Wineries and Estates in Geneva NY on March 27 2027 with a T shirt, cider pour, medal and donut.