Trail Running calendar near Englewood Cliffs 2026-2027

NYRR Cross Country Series #2 is a scored 5K cross country race at Van Cortlandt Park in the Bronx on October 4, 2026. The event includes a free Rising NYRR kids program and a member standby registration option.

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 the Rocky Point pine barrens using a 10.48 mile loop repeated to cover distances from 10 to 150 miles, supported by two stocked aid stations 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.

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.

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.

Scary Rat Race is a four-mile off-road trail run at Spring Meadow Golf Course in Allaire State Park on October 11, 2026. The event uses hand-held timing, includes a free drink ticket and a finisher gift, and offers t-shirts and other items..

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.

A non-profit off road 5K at the Hudson Highlands Nature Center in Cornwall NY on October 17, 2026. The route passes ponds, meadows, grassy paths and wooded trails while supporting nature-based education; 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.

An off-road 50K starting at Guilford Lakes School that runs through linked woodland preserves on rocky forest road and single-track terrain. The course avoids repeated loops and recommends recent marathon-level experience.

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.

The 4th annual Chesterfield FALL Terrain 5K at Fenton Lane Park on October 18, 2026 features a 5K run/walk and a 1 mile Fun Dash, supports local charities, offers custom race shirts and age group awards.