Trail Running calendar near Garrison 2026-2027

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.

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 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.

Mountain trail race at Camelback Resort on October 4, 2026, run on a 2.5 mile loop with just under 900 ft of climb per loop. Options include 2.5, 5, 10 miles, a 10 mile team relay, ruck division and chip timing.

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 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.

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..

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.

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.

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 trail 5K at Blydenburgh County Park on October 11, 2026 with a shaded mixed-surface course, participant tee, on-site refreshments and parking details. A virtual 5K option runs Oct 11 to Oct 18 and includes a shirt and bib name.