Trail Running Calendar New York 2026-2027

A community 5K on September 27, 2026 in Dolgeville along the Greenway Trail. Registration has a $25 fee with children under 12 free; proceeds fund free sports equipment for local youth.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

A scored 5K cross country race at Van Cortlandt Park in the Bronx on September 27, 2026, part of NYRR's fall series; includes free youth races for ages 2 to 18 and awards for top finishers across divisions.

Experience a rugged trail race through the Adirondack forests and wetlands of Amy’s Park. Enjoy scenic views and a community after party at a local brewery while supporting land conservation for Lake George.

A timed endurance event in Cohoes, NY offering 6-hour, 3-hour and 1-hour solo options plus 6-hour relays, organized by Flutters of Hope Inc to raise awareness and funds for people affected by eating disorders.

A 50 kilometer trail ultramarathon on October 3, 2026 in Kattskill bay, NY, starting and finishing at Camp Chingachgook with about 9,000 feet of climbing across multiple Lake George peaks. Prior ultra-trail experience is required.

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.

A 3 mile open unattached race in Genesee Valley Park, Rochester, included in the 60th McQuaid Invitational. Online entry runs July 5 to October 2 with a $15 pre race fee and $20 cash on race day.

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.

On October 4, 2026 the Highlander Heavy Half in Cold Spring, NY is a 13.7 mile trail race with roughly 4,000 ft of elevation gain through the Hudson Highlands. A portion of proceeds supports the 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.

Run a scored 5K race through the scenic trails and varied terrain of Van Cortlandt Park. This Bronx event features divisions for all adults and free youth races for ages 2 to 18.

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.

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 Rocky Point centered on a 10.48 mile loop, offering distances from 10 miles to 150 miles with two stocked aid stations, crew and pacer support, and weekend long cut-offs for all races.

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.

A trail race weekend in October 2026 near Hemlock, NY featuring a full marathon, a 15K and a point to point 5K across single track and gravel, with proceeds directed to local trail maintenance.