Trail Running Calendar New York 2026-2027

Experience a monthly trail running series through the scenic landscapes of Mendon Ponds Park. Each event features timed races of varying distances followed by a social gathering with pizza and drinks.

An ultramarathon in Van Cortlandt Park featuring an initial flat lap plus ten cross country loops, stocked aid stations, drop bag access, and finisher awards including a medal, singlet, meal and post race beer.

A muddy obstacle-course festival in Deansboro, New York offering 5 mile, 5K and kids runs plus live music and local brews. Proceeds support the Barden Adventure Scholarship and other charitable efforts.

Run on the smooth, paved Black River Trail overlooking the water in Watertown, NY. Choose from a 5K, 10K, 15K combo, or try the ruck division. The event supports local transportation services and offers a post-race gathering at a nearby bre..

The A Run to Remember will take place in Red Hook on Saturday 2 May 2026. You can run between 5 and 10 kilometers.

Rock The Ridge is a fundraising trail event at Mohonk Preserve on May 2, 2026. Options include a 50 mile ultra, a 26.2 mile trail marathon and relay teams, with proceeds supporting conservation and education.

Trail races at Bear Mountain State Park on May 2, 2026 include 10K, half marathon and 50K over singletrack with technical sections, rolling climbs, tree cover, rocky and muddy terrain and occasional stream crossings.

Run a flat one mile course in Van Cortlandt Park while wearing your own inflatable costume. This unique Bronx event supports charity and takes place during a local ultramarathon for a high energy atmosphere.

A technical trail half and full marathon at University Settlement Camp in Beacon, NY on May 3, 2026, featuring steep, exposed climbs and substantial elevation gain with official aid stations and strict cut-off times.

Experience the natural beauty of Mendon Ponds Park with a choice of 13 mile and 5 mile trail races. Enjoy a festive atmosphere featuring a post race BBQ feast at Stewart Lodge.

A scenic 5K trail run and kids race at Holimont Ski Resort in Ellicottville on wooded mountain paths. All racers get a post-race party and tacos; 5K participants receive a Sasquatch Stomp t-shirt. Proceeds support the Ellicottville Great Va..

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..

Mind The Ducks is a 12-hour ultramarathon on a looped course in Webster, NY. Runners aim to complete as many 1.01203-mile laps as they can. The event supports a local charity and is organized by a running club.

Test your endurance at Greek Peak with a single day walking and rucking challenge through the scenic Finger Lakes foothills. Choose between distances ranging from 7 to 28 miles on a beautiful 1480 foot elevation loop.

This community trail run on Clausland Mountain honors caregivers and supports mental health and sobriety causes. Participants take on a 3.75-mile historic course, receiving a medal in an event focused on gathering, not competition.

A 3.5 mile obstacle course across 100 acres of wooded terrain with timed elite and age group heats, a multi lap endurance heat, and untimed open waves that include an event shirt and medal.

The Towpath Trail Run in Saint Johnsville offers a flat, paved course for a 10K and a 5K run/walk. Professional timing ensures accurate results. The event is scheduled for May 9, 2026.

Run for a cause at the Bruynswick Winery Run, a 6k cross-country race benefiting the Ulster County SPCA. Enjoy a scenic course at the foot of the Shawangunk Ridge, with music, drinks, and a chance to meet shelter animals. Free children's da..

A 5K trail run through the orchard at Indian Ladder Farms on May 10, 2026, with a hard cider mimosa provided after the finish and non alcoholic options; top 1st to 3rd place finishers aged 21 and over receive craft cider bottles.

Experience the beauty of Letchworth State Park through a series of trail races ranging from a 5K to a full 26.3 mile marathon. Choose a solo challenge or join a relay team for a weekend of trail running in Western New York.