New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 141 exciting trail runs across the region. Find your next trail run in New York below and join the trail community at these great events!
May 2027
Chip timed 5k at Millbrook Vineyards & Winery on May 15, 2027 with a grassy two lap course, race swag, a pour of wine at the finish, and age group awards.
A 5K run and walk at Bethpage State Park with winding soft trails, live timing, free finish line photos, and awards for top male and female overall.
A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarships.
Trail races at Green Lakes State Park on May 16, 2027, with 10 mile and 5 mile beach-to-lake routes, water aid, awards, and support for NAMI Syracuse.
A community 5K trail run and walk at Blydenburgh County Park with on-site amenities, a virtual option, and donations benefiting the Never Stop Running Foundation.
A chip timed 5K at Brooklyn Cider House on May 22, 2027 combining a run or walk with local cider, a shirt, medal, donut and a pour of cider.
A marathon and half marathon at Whiteface Mountain on May 22, 2027, featuring alpine and flume loops with technical footing and significant elevation gain.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
Timed endurance event at Holiday Valley on May 30, 2027 offering 7, 14, 21 and 28 mile trail options plus weighted divisions.
A Last Runner Standing style event on May 30, 2027 in Powder Mills Park with repeated one mile loops, 25 cutoff laps, a final all out lap, and family friendly facilities.
June 2027
Two-course trail event at Rockland Lake State Park with a fully accessible paved 5K loop and a rugged 10K mountain route rising 1,300 ft to Hook Mountain Summit.
Trail ultramarathons near Ithaca, NY offering 50K and 50M courses with extensive singletrack, waterfalls, staffed aid stations, and drop bag support.
A Backyard Ultra at Trenton Fish and Game Club with a 3 1/3 mile loop every hour, a 30 hour limit, personal 12' x 12' runner areas and milestone patches.
Trail races in Roxbury NY on June 6, 2027 include a 6.5 mile mountain race with 3,500 ft gain and a 5k with steep early climb and downhill finish.
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
Trail races at Robert Treman State Park on June 6, 2027, with a half marathon, 10K and 5K over wooded singletrack and on-course support.
YMCA Race Weekend in Central New York features a sprint triathlon, duathlon, aquabike, aqua run and an 8K trail race while raising funds for YMCA charitable programs.
A community 5K and one mile family walk at Camp Edey in Bayport supporting Girl Scouts of Suffolk County programs and scholarships.
Point to point half marathon from Trumansburg to Cass Park in Ithaca with a net descent, trail sections, aid stations, shuttle service, and race day amenities.
A roughly 45 mile trail ultra in Letchworth State Park using both sides of the gorge, mostly off road, with six aid stations and stretches up to eight miles between them.