Trail Running Calendar New York 2026-2027

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

A four mile trail race through Irvington Woods on October 4, 2026, with varied terrain including climbs and stairs; start and finish at Irvington High School. Registration runs March 15 to September 4 with a $40 fee.

A 3.1 mile trail race at the Great Swamp Conservancy habitat center in Canastota NY on October 4, 2026. The course runs on natural trails and crosses a country road; registration opens July 15 and the fee is $20.

A 13.7 mile trail race in Cold Spring, NY on October 4, 2026, featuring about 4,000 ft of climbing through the Hudson Highlands during peak foliage. The event is an UTMB Index Race and supports the NYNJTC.

An off pavement 5 km trail run and walk through Winona Forest in Mannsville, NY, limited to 100 participants, with timing, awards and a post race BBQ. Proceeds support Friends Forever Animal Rescue and leashed dogs are welcome.

NYRR Cross Country Series #2 is a scored 5K cross country race at Van Cortlandt Park in the Bronx on October 4, 2026. The event includes a free Rising NYRR kids program and a member standby registration option.

Runners climb the Empire State Building's 86 flights and 1,576 stairs to the observatory in this New York tower race on 10/06/2026. Multiple entry categories are offered with different registration windows and fees.

A four day trail event in the Rocky Point pine barrens using a 10.48 mile loop repeated to cover distances from 10 to 150 miles, supported by two stocked aid stations and crew and pacer rules.

The Trailwagger is an October 2026 trail event at Gilbert Lake State Park in Laurens, NY with 3 mile, 5 mile, combined 8 mile and two person team options plus a dog stroll. A portion of proceeds supports Super Heroes Humane Society.

Trail runs of 10K and 23K through singletrack and dirt roads in Danby State Forest with views from the Thatcher Pinnacles. The course features marked turns, aid stations, and varied elevation and footing.

Trail races near Hemlock and Canadice Lakes in Springwater NY offering 5K, 15K and a full marathon. Courses include technical single track, a steep 0.5 mile descent on the 5K and two 800 ft climbs on the marathon.

An off road run at Holiday Valley Resort in Ellicottville on October 10, 2026, with 4 mile and 8 mile options. Entry is limited and Ellicottville Brewing will provide after race refreshments.

A single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

A scenic trail 5K at Blydenburgh County Park in Smithtown, NY on October 11, 2026, with in-person and virtual options, a free kiddie dash, event tee, refreshments, and age group recognition.

Run a 5K through the private 157 acre Rochester Rotary Sunshine Camp on a mix of dirt trails and paved paths. Enjoy the post race Beer Fest and support accessible camping for children with disabilities.

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

A spooky themed 3.1 mile run in Mendon, New York on the Lehigh Valley Trail with a costume contest, awards, a post race party at the Cottage Hotel Restaurant, and a virtual entry option; proceeds support David's Refuge.

Test your endurance at Nocturnal 12 a night-themed twelve hour fixed time race on a flat paved path. Walkers and runners can complete as many laps as they choose on this flexible out and back course.

A non-profit off road 5K at the Hudson Highlands Nature Center in Cornwall NY on October 17, 2026. The route passes ponds, meadows, grassy paths and wooded trails while supporting nature-based education; children under 18 run free.