Trail Running Calendar New York 2026-2027

A community wellness event at Sprague Brook County Park on September 12, 2026 featuring a 5K trail run and a 2 mile non timed walk, with proceeds supporting the Bread of Life Outreach Center and keepsake blankets for early registrants.

Experience an outdoor adventure at Everest Park featuring a four mile obstacle course with forty natural and man made challenges. Families can choose between the full mud run or a specialized mini course for younger children.

Experience a non competitive trail run or walk through 63 acres of scenic trails at a therapeutic riding facility. Choose between 1km and 5km distances and earn a completion medal while supporting a local nonprofit.

A dog friendly 5K community run and walk at Campground Adventures in Hinsdale, NY on Saturday, September 12, 2026. Fifty percent of proceeds support the Cattaraugus County SPCA and the event features scenic trails and local vendors.

A community fundraiser at Mendon Ponds Park with in-person and virtual 5k options plus a Trail X Challenge and a 10k combo. The event supports ROCovery and includes event swag and packet pick up dates.

A 5K and 10K trail run in Letchworth State Park on September 13, 2026 featuring woodland courses, finisher medals, a post-race celebration at Trailside Lodge, and timed results with downloadable certificates and photos.

An inaugural trail festival at Greek Peak Mountain Resort in September 2026 featuring multiple mountain races, a kids mile, and a dog friendly 5k. Night races require headlamps and an Uphill 1k climbs the Iliad slope.

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.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

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.

A trail running event in Brookfield, New York offering 5k, 15k and 50k courses through Charles E. Baker State Forest; the 50k uses multi loop format, has over 4,800 feet of gain and a nine hour cutoff.

A multi-race trail festival at Lakeside Park in Pawling, NY offering timed 24, 12 day, 12 night, 6 and 3 hour events on an about 1.68 mile loop with on-course aid, music, and finisher medals.

A USATF sanctioned trail ultra near Upper Nyack, NY offering a 50 mile race with about 9,700 feet of gain and a 27 mile mountain marathon. The course uses a 4 mile out and back plus repeated 11.5 mile loops along the Palisades ridge and Hud..

A roughly 100 km trail ultramarathon around Morgan Hill State Forest with about 10,286 ft of elevation and seven aid stations. The route follows mostly single track and requires offline navigation and self-sufficiency.

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.

Trail run and walk at Huyck Preserve in Rensselaerville NY on Saturday September 19 2026. Routes of 2 5 and 8 miles pass Lake Myosotis and a historic racetrack while raising funds for local organizations.

A scenic 5K cross-country race and a 2 mile fun run and walk at Crown Point State Historic Site. The event includes awards for 5K participants, on-site facilities and a waived registration fee for students 18 and under.

A scenic five mile memorial run and virtual five mile option in Hinckley, NY, with a kids fun run included; proceeds fund a memorial scholarship for students pursuing medical studies.

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 5K trail run on Bella Rose Vineyard grounds in Lewiston with a stemless wine glass and complimentary wine tasting for participants 21 or older. The event features professional timing, finish line photos, music, and on site parking.