Trail Running Calendar New York 2026-2027

Test your endurance at Kissing Bridge with this twelve hour backyard ultra style event. Runners tackle a three mile loop every hour on the hour until the final race determines the winner.

61st McQuaid Invitational at Genesee Valley Park features an open 3 mile unattached race alongside invitational high school and junior high races, with online registration.

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 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.

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.

Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.

A fall trail 5K in Winona Forest that supports Friends Forever Animal Rescue, featuring an all-off-pavement course, on-site timing, awards, a post-race BBQ, and the option to add a donation during registration.

A scored 5K cross country race at Van Cortlandt Park in the Bronx on October 4, 2026 with live app tracking and on site awards.

Trail runs of 3.1 miles and 6.2 miles take place at Genesee County Park and Forest on October 4, 2026. Proceeds support ACORNS and a portion will go to breast cancer research.

A tower run up the Empire State Building's 86 floors and 1,576 stairs in New York with multiple entry categories and specific registration windows.

Multi-day trail event in Rocky Point, NY on a 10.48 mile loop repeated for distances up to 150 miles, with two stocked aid stations and crew support.

Trailwagger at Gilbert Lake State Park on October 10, 2026 features 3, 5 and combined 8 mile courses, a two person team division, and a dog stroll. A portion of proceeds supports a local animal shelter.

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 Canadice and Hemlock lakes offering marathon, 15K and a point-to-point 5K with technical single-track sections and two major climbs.

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.

Community 5K and a 0.5 mile youth run at Pitney Meadows Community Farm on October 10, 2026. The mixed surface, spectator friendly course runs on grass and stone dust and raises funds for the farm's programs.

Experience a scenic 5K run on the historic carriage roads of Rockefeller State Park Preserve. Support trail maintenance while enjoying autumn views of Swan Lake and rolling pastures.

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 **5K** trail run and walk at Blydenburgh County Park on October 11, 2026 with in-person and virtual options. Participants receive a race tee, on course hydration and age group recognition while proceeds benefit a local running foun..