Trail Running Calendar New York 2026-2027

Community trail events at the John Jay campus in Cross River, NY featuring a 5k trail race, a 4k Jay Walk, and a 200 m Kids Jay Dash on the track. Woodland sections include hilly terrain and finishes are on the contest field.

A community trail event in Irvington on April 12, 2026 featuring a 5k trail run and a 0.6 mile kids 1K for ages 10 and under, with a portion of proceeds supporting the Irvington Bulldog Booster Club.

Trail races at Green Lakes State Park in Fayetteville, NY offering 50km, 20 Miler, and 10 Miler on an approximately 10 mile loop with varied terrain and about 1,300 feet of elevation gain.

A point-to-point 50K and 25K on the Long Island Greenbelt Trail on April 18, 2026, featuring marked singletrack, five stocked aid stations, drop-bag options for 50K, and a two-hour trail-work requirement for entrants.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry at Mercy University for a scenic 7.5k on the Croton Aqueduct Trail. Celebrate Mercy's 75th, snag a commemorative shirt, and support the Mav Market.

A technical *20K* trail run through Hi Tor Wildlife Management Area near Naples, NY, with steep elevation changes, varied terrain and wildlife encounters; entry is limited to 200 runners and a clear refund schedule applies.

Join the Brooklyn Cider House Spiked Apple 5K in New Paltz on April 19, 2026 for a chip timed run or walk. Enjoy a tee, cider pour, donut and a finisher medal that doubles as a bottle opener for a festive post race celebration.

The Brookhaven Trail 15K Run will take place in Wading River on Sunday 19 April 2026. You can run between 4 and 15 kilometers.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 is a rugged trail test on the Shawangunk Ridge with a 25K and a 10 mile option over steep climbs and technical singletrack. Field capped at 150 and proceeds benefit Run Wild.

A 15K trail race at Grafton Lakes State Park covering about 9.3 miles with 900 ft of elevation gain. The technical yet runnable spring course can be muddy and is described as accessible for new trail runners.

A community race day in Elizabethtown, NY featuring a 13.1 mile half marathon, a new 5K trail race, and a kids 5K for ages 10 and under. Proceeds benefit Elizabethtown Community Hospital and local health programs.

Leatherman's Loop is a 10k trail race at Ward Pound Ridge Reservation in Cross River, NY on April 26, 2026. Entry is by lottery and the race is USATF sanctioned; registration includes the park entry fee.

A community 5K on April 26, 2026 in Croghan NY offering walk, bike, and run options, with a pancake breakfast included and no official timing.

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.

DENFIT ULTRA at Buffalo Ski Center is a 10 km ski slope loop with 50k or 100k options, offering big elevation and possible snow. Parts are unlit so headlamps are required and finishers earn medals and custom spears.

Join the 5th annual Black River Trail Run on May 2, 2026 in Watertown, NY for a scenic, smooth and flat paved course that hugs the Black River. Choose 5K, 10K, combo, ruck or virtual options while supporting the Volunteer Transportation Cen..

Run to Remember on May 2, 2026 in Red Hook NY offers scenic 5K and 10K trail runs plus a 5K walk through meadows, orchards and forest. Honor loved ones and enjoy community spirit with cash prizes for top finishers.

A fundraising trail event in the Shawangunk Mountains on May 2, 2026 offering a 50 mile Ultra Marathon, a 26.2 mile Trail Marathon and two to four person relays. Proceeds support Mohonk Preserve conservation, education and stewardship.

Trail races at Bear Mountain State Park near New York City on May 2, 2026, featuring 10K, half marathon and 50K options across singletrack with rocky, rooted, and forested sections offering occasional views.

A technical trail event near Beacon, NY on May 3, 2026 offering half and full courses with steep exposed climbs, significant elevation gain, aid stations, limited on-site camping, and a participant shirt and finisher item.