Trail Running calendar near Garrison 2026-2027

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 an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

Test your limits on a flat one mile loop at the Sussex County Fairgrounds. Choose from 6 to 72 hour timed races or certified marathon and 50K distances with full kitchen and shower access.

A 15 mile trail event at Mohawk Mountain Ski Area in Cornwall, Connecticut on October 3–4, 2026, offering 7,140' of elevation gain and a 12 hour time limit. Participants may run, hike, or walk; the event is produced by a veteran owned compa..

A 30 hour trail ultra at Roosevelt Forest with a 2.23 mile loop, marked course, multiple distance options, and a 100 mile finisher buckle. Aid is centered at the pavilion and one registered pacer is allowed per runner.

A six-week adult cross country series in Monmouth County featuring six 5K races at local parks, with team and individual scoring and age group awards. Registration options include a full-series fee or per-race entry, with event-day registra..

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.

Mountain trail race at Camelback Resort on October 4, 2026, run on a 2.5 mile loop with just under 900 ft of climb per loop. Options include 2.5, 5, 10 miles, a 10 mile team relay, ruck division and chip timing.

The Haystack Mountain Challenge on October 4, 2026, features a 5K, 10K and a half marathon across Barbour Woods and Haystack Mountain, with steep climbs, private trail sections, a cupless policy, water stations and on site refreshments.

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.

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 multi-distance trail race in Rocky Point, NY held October 9–12, 2026, using a 10.48 mile loop for all distances. The event features two aid stations with Hylē Hydration, course flagging, night race options, and crew and pacer rules.

A family friendly trail event on October 10, 2026 in Wilton CT offering a 5K and a short accessible run or walk, with participant perks and support for employment initiatives for people with disabilities.

Experience a trail race at Mohawk Mountain Ski Resort featuring distances from 5k to a full marathon. Run through fall foliage on a course that includes steep ski slopes and the scenic Mohawk State Forest.

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.

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.