Trail Running Calendar New York 2026-2027

A four mile cross country race in Riverdale and Van Cortlandt Park with an informal kids fun run, finisher hat, awards for top finishers and masters, and post race refreshments; proceeds benefit the FDNY Foundation.

A trail 5K at Blydenburgh County Park on May 23, 2026 with in person and virtual options plus a free kiddie dash. The route mixes pavement, dirt roads, and hard packed trails and includes post race hydration and refreshments.

Experience the trails of Highland Forest County Park with 10 mile, 20 mile, and 50K distance options. This event features technical terrain and significant elevation gain through forests and logging lanes near Fabius.

The Mills Miles is a Last Runner Standing event at Powder Mills Park in Pittsford, NY featuring repeated one mile loops with time cutoffs, a final all out lap, post-race BBQ and awards, and fundraising support for TrailsROC.

A four mile road and trail race in Forest Park with start and finish at Victory Field track. The event is limited to 500 entrants, includes chip timing, technical shirts for pre-registrants, finisher medals, cash awards and age group trophi..

A single-day endurance walk at Holiday Valley, Ellicottville on May 24, 2026, offering 7, 14, 21, or 28-mile options with optional 10/20/35 lb rucking, a 10-hour finish window, well-marked trails, and regular aid stations.

A four race 5 km trail series at Cole's Woods in Glens Falls across Tuesdays in May, with a 20 km challenge for those who complete all four events. Entry fees, T shirt allocation, awards and proceeds benefiting the Glens Falls Youth Center..

A budget-friendly midweek trail series across four Monroe County parks offering single-race entries or an all four series option. Features chip timing, a post-race cookout, series scoring and awards plus a custom hat for series entrants.

Six 5K cross country races take place at Van Cortlandt Park from May 28 to July 30, 2026, on the classic Tortoise and Hare course. The final three evenings include free half mile kids runs, weekly awards and post race raffles.

A trail ultramarathon at Robert Treman State Park on May 30, 2026, offering 50K and 50 Mile courses with substantial elevation. Routes are mostly singletrack and pass waterfalls, stone stairs, multiple aid stations, and managed drop bag sup..

Trail run in Boutwell Hill State Forest near Cherry Creek New York offering 6k, 12k, 26k and 52k routes. The event raises funds for the Chautauqua County Equestrian Trail System and includes aid stations for the longer distances.

ENDURE Last Man Standing in Bethpage State Park asks runners to repeat a fixed 4.2 mile loop each hour; finish within the hour to continue. Laps continue with progressively shorter cutoffs until one runner remains or the event window ends.

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

A two-day outdoor obstacle event in Wallkill, NY offering adult sprints and multi-lap endurance races plus kids’ sprint and 1 km courses, finisher medals, age-group awards, a nonprofit Teddy Bear Crawl presence, and on-site youth fundraisin..

A backyard ultra on May 30, 2026 at Trenton Fish and Game Club where runners repeat a 3 1/3 mile loop each hour until one remains or a 30 hour limit is reached. Milestone patches and live online tracking are provided.

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

Lucifer's Crossing on May 31, 2026 in Robert Treman State Park features trail 5K, 10K and a 13.2 mile half that pass through Lucifer Falls gorge and Finger Lakes singletrack.

A four-week, 90-minute trail running series for runners comfortable with about 3 miles. Sessions cover warm-ups, guided runs, hill and footwork drills, gear and safety, and include trail socks and gifts.

A weekly Thursday evening trail run and mountain bike race series at Mt Van Hoevenberg, held June through August, with age divisions, set distances, weekly raffles and series awards.

Trail runs in Naples NY with a rugged 25K single loop around the Cumming Nature Center and Honeoye Inlet Wildlife Management Area and a more runnable 10K. Proceeds support environmental education at the RMSC Cumming Nature Center.