Trail Running calendar near Hauppauge 2026-2027

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

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

A community 5K and 2 Mile Walk at Garrett Mountain on October 11, 2026, with virtual and Tot Trot options; proceeds benefit the Fred Torres Memorial Scholarship Fund supporting Clifton High School athletes.

Trail run at Jungle Habitat in West Milford NJ with looped singletrack, fire road and paved sections, cupless aid stations, wooden finisher plaques and a post race party.

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.

On 10/10/2026 the Gemstone Sparkle Sprint 5k at Gemstone Farm in Wilton CT features a timed trail 5k, an accessible stroller run, live music, food and access to the farm, with proceeds supporting The Prospector's mission.

A community 5K at Duke Island Park on October 10, 2026, run on a flat, paved trail alongside the Raritan River. Proceeds support Family & Community Services of Somerset County, which provides mental health and addiction services.

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.

Trail running at Mohawk Mountain Ski Area with 5K, 10K, half and marathon routes on ski slopes and state forest, cupless aid stations and finisher medals.

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.

Scary Rat Race is a 4 mile off road trail run at Spring Meadow Golf Course in Farmingdale, NJ on October 11, 2026, featuring hand held timing, a finisher gift, free registration, and event merchandise for sale.

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..

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 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.

Loop-based running event at Livingston Memorial Oval on October 17, 2026 offering marathon, half-marathon and a Last Person Standing timed challenge.

A technical trail event in Harriman State Park offering 13.1M and 10K on rugged singletrack with steep climbs, limited to 175 participants.