New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 168 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
A Thanksgiving Day 5K run and walk at Alley Pond Park with a virtual option, a free kiddie dash, and donations benefiting the Never Stop Running Foundation.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
A Thanksgiving morning 5K and one mile fun run on Cazenovia Gorge Trail with chip timing, prizes, and a food collection.
A community 5K trail run at Bethpage State Park on November 28, 2026, with in person and virtual options, a free kiddie fun run, bib mailing, shirts, and postrace 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.
Trail 5K at Belmont Lake State Park on November 29, 2026 with a cash raffle where 50% of 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.
January 2027
Winter trail run of about 10k at Harriet Hollister Spencer State Recreation Area with likely snow, no aid stations, and a post-race gathering at Birdhouse Brewing.
Winter trail race in Ontario County Park with 4, 8, and 12 mile options, a heated lodge, pancake refreshment, and winter-focused gear recommendations.
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.
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 finisher me..
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.
A 5K trail run and free kiddie clover fun run at Bethpage State Park with a virtual option, finisher shirts, post race refreshments and age group awards.
April 2027
A scenic 5K at Bethpage State Park with in person and virtual options, refreshments, bib mailing, and age-group recognition; proceeds support the Never Stop Running Foundation.
Mountain trail races at Bear Mountain on April 3, 2027 offering 13.1 mile, 10K and 10K ruck on rugged technical singletrack with significant elevation gain.