Trail Running Calendar New York 2026-2027

A rugged trail marathon in Shandaken, NY with a point to point course through the Slide Mountain Wilderness and nearly 7,000 feet of vertical gain. Proceeds support Run Wild, Inc.

An eight hour fixed time race and relay on a flat **3.45 mile** out and back trail next to Dryden Lake. Solo and team divisions, a single well stocked aid station, and optional 0.4 mile mini loops in the final hour.

The Morgan Hill Trail Races will take place in Fabius on Sunday 27 September 2026.

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.

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.

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.