New York
New York Trail Running Calendar 2026-2027
Explore the best trail runs in New York for 2026-2027! Our updated list features 174 exciting trail runs across the region. Find your next trail run in New York below and join the trail community at these great events!
September 2026
An annual fundraiser at Mendon Ponds Park offering road and trail 5K options, a trail 5K with challenge stations, a virtual 5K in September, and a 10K combo. Proceeds support ROCovery recovery programs and community services.
Trail runs in Letchworth State Park on September 13, 2026 offering 5K and 10K woodland courses with on-course water, chip timing, and post-race refreshments.
Trail running festival at Greek Peak Mountain Resort featuring multiple distances, night runs, a dog-friendly 5k, and family activities.
An obstacle and fitness race on September 13, 2026 in Fayetteville, NY featuring a roughly 3 mile course with about 23 first responder inspired challenges, including Search & Rescue, Hose Drag and timed mental focus tasks.
Multi-day timed ultras at Shortsville Reindeer Farm on a one mile grass and trail loop. Multiple timed options, an on-course aid barn, and belt buckles for finishers who complete 100 loops; proceeds support ROCovery Fitness.
Trail races in Brookfield New York offer a 5k, 15k and a 50k ultra on truck and horse trails; the 50k includes 4,800+ feet of vertical gain and a nine hour cutoff.
Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.
A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.
A 100km trail race in Morgan Hill State Forest, Tully NY, mostly single-track across four counties with a 20 hour cutoff and required offline navigation.
A community 5K and 10K on the Keuka Outlet Trail in Penn Yan with start and finish at Cascade Falls. Courses pass Seneca Mills Falls and the 10K reaches the former Fox Mills site; shirts and medals included.
A community trail run and walk on September 19, 2026 at Huyck Preserve offering 2, 5, and 8 mile routes through lake, historic track, and waterfalls, with proceeds shared by the Huyck Preserve and Rensselaerville Library.
Scenic 5K cross-country and a 2 Mile fun run/walk at Crown Point State Historic Site supporting online safety awareness and the NYS Parks wellness challenge.
A community 5K run and a children’s 1 mile fun run at Schodack Town Park on September 19, 2026, raising funds for Hope House. Entry fees include 5K $30 and children free with parents running $30.
A 5K cross country race at Pine Grove Middle School in East Syracuse on 19 September 2026, run on a varsity XC course with mostly trails and grass; registration runs from March 7 to September 18, 2026.
A 10th annual community 5K at Camphill Village Copake on September 19, 2026, featuring woodland and pasture trails plus a village Ring Road for walking, strolling, or rolling.
A community memorial run in Hinckley, NY offering an in-person five-mile trail run/walk, a virtual five-mile option, and a kids fun run; proceeds support a memorial scholarship for students pursuing medical training.
A one mile loop elimination challenge in Webster NY on September 20, 2026 where runners must meet shrinking time cutoffs each mile; finishers receive a medal and category pins, with cash prizes for top male and female.
A charity running event at Green Lakes State Park on September 20, 2026 with 8K and 5K races, a free kids fun run, a 5K lake trail route, and a 2 Mile trail walk, plus shirts, awards, aid stations, and free ice cream.
A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.