Trail Running calendar near Woodland Park 2026-2027

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.

The Fred Torres Memorial 5K will take place in Woodland Park from Sunday 4 October 2026 to Sunday 11 October 2026. You can run 5 kilometers.

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.

Experience a USATF sanctioned endurance event on a flat paved loop in New Jersey. Choose from 12 to 48 hour individual or relay options and earn a custom buckle for completing 100 miles.

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.

A point to point trail run in Slatington, PA on October 10, 2026 featuring a 10 km race and a 2 Mile Scramble with single track, technical sections, and a final 1,000 foot ascent to the finish.

Muleskinner runs along canal towpaths in Bucks County on October 10, 2026, with distances from a 13.1 mile half to a 50 mile ultra. The event is cup free, offers aid stations and nearby tent camping at Tinicum Park.

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 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.

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.

A non competitive winter running series of six loops totaling 66 miles along the Delaware River in NJ and PA from October 2026 to February 2027. Limited to 100 registrants, includes aid stations and a handmade finisher award.

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.

Big Bear SquaTch South is a trail running event at Harriman State Park on October 18, 2026 offering a technical half marathon and a 10K with steep climbs, marked courses, aid stations, and capped fields.

A Halloween themed event on Clinton Road in West Milford, NJ offering a 1 mile Zombie Crawl plus 5k and 10k races. The course features zombie volunteers, themed aid stations, and a finish line festival with awards and a costume contest.

Trail and 5K races at Hillside Park on October 18, 2026, benefit a free mammography program. A kids fun run for ages 5 to 12 is included, with chili and vegetarian food and timing by Compuscore.