Trail Running calendar near Milford 2026-2027

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.

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.

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 point to point trail race on October 10, 2026 in Slatington, PA featuring a new 10 km course that finishes 1,000 vertical feet above the Lehigh Gap. The route includes singletrack, technical sections, and varied terrain.

Trail-based multi-distance races on the towpaths in Upper Black Eddy, PA, with aid stations, onsite tent camping, awards, and donations to local preservation groups.

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.

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 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.

The Livingston Oval Marathon will take place in Livingston on Saturday 17 October 2026. You can run between 21 and 42 kilometers.

A community 5K and 1 mile fun run and walk at Tamaqua Area High School on October 17, 2026, raising funds for a memorial scholarship.

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

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.

Trail ultramarathon in Titusville, NJ with 50K and 25K courses that start and finish at Washington Crossing Park. The 50K features technical Rock Hopper trails and multiple aid stations.

A trail-based 5K and family 1 mile fun run in Poricy Park with a Halloween costume theme and prizes, raising funds for 180 Turning Lives Around. Options include a timed 5K, a fitness walk, and a family fun run.

A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.

An age-group graded 5.5-mile trail race at Frances Slocum State Park on October 25, 2026, run mainly on grass and earth. Pre-registration is required; the entry fee is $10 and online registration closes October 23.