Trail Running calendar near Rocky Point 2026-2027

A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.

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 a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

A 15-mile trail event at Mohawk Mountain Ski Area in Cornwall, CT with 7,140 feet of elevation and a 12-hour limit; participants may run, hike, walk, or compete in a relay, with registration listed as free for the stated window.

A 30 Hour looped trail event at Roosevelt Forest in Stratford CT on October 3 and 4, 2026 offering distances from 26.2 miles to 100 miles on a 2.5 mile loop with central aid at the pavilion and a finisher buckle for 100 miles.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

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 26.4-mile trail marathon in Ashford, CT, on the Nipmuck Trail featuring rocks, roots, mud, and wood bridges, with a two-person relay option and race shirts available before September 12.

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.

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.

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.

Jungle Escape is a trail running event at Jungle Habitat in West Milford NJ on October 4, 2026. Routes include a 13.2 mile half marathon plus, a 6.6 mile 10K plus and a 3.4 mile 5K plus with marked trails and cupless aid stations.

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 Rocky Point centered on a 10.48 mile loop, offering distances from 10 miles to 150 miles with two stocked aid stations, crew and pacer support, and weekend long cut-offs for all races.

A third annual trail event on October 10, 2026 in Wilton, CT featuring a 5K trail race and an accessible short run/walk, event T-shirts, food and on-site access to farm grounds; proceeds support employment opportunities for people with disa..

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.

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.