Trail Running calendar near Poughkeepsie 2026-2027

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

Repeat a 3.3 mile out and back up the Tower Trail to the Observation Tower at Sleeping Giant. Runners choose a four hour or eight hour format, carry their own hydration, and complete as many laps as they can within the time limit.

Trail races at South Mountain Reservation feature 5K, 10K and 13.1 miles on looped courses over fire roads, single track, hills and pavement, with aid about every three miles and race day registration available.

A looped ultramarathon in Prospect Park, Brooklyn offering 50 mile and 50 kilometer options. The course uses 3.33 mile loops and includes on course hydration and a potluck style aid station.

A forest trail 5K in Roosevelt Forest, Stratford, CT on December 19, 2026, where participants may run, jog, hike, or walk in costume. Awards go to the three fastest men and women and all finishers receive a commemorative item.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.

The Squatchy Onesie Fest “5K-Marathon” will take place in Mahwah on Sunday 14 February 2027. You can run 5 kilometers.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

A timed loop event at Livingston Oval where runners cover as many laps as possible in one, three, six or twelve hours on a USATF certified flat course, with aid stations and awards for top male and female finishers.

The Squatchapple - West Orange, NJ will take place in West Orange on Saturday 6 March 2027. You can run between 11 and 50 miles.

A 5K trail run and walk at Bethpage State Park with a free kiddie run and virtual option. On-course hydration, post-race refreshments, age-group recognition, and proceeds support the Never Stop Running Foundation.

A community 5K run and free kiddie run on the soft trails of Bethpage State Park, supporting the Never Stop Running Foundation. The event includes in-person and virtual options, refreshments, bib mailing, and age-group recognition.

A mountain trail event at Harriman State Park on April 3, 2027 offering a half marathon, a 10K and a 10K ruck on rugged technical trails with significant elevation gain. Entry is capped at 400 and proceeds support trail maintenance.

Trail races at Sleeping Giant State Park in Hamden, CT offering 25K and 50K loops. The 25K has 3,000 plus feet of vertical gain and varied terrain from carriage roads to steep rock scrambles, with aid stations and postrace food available.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY with mixed trail surfaces, dog friendly rules, on site amenities, live results and proceeds supporting Last Chance Animal Rescue.

A mountain obstacle race weekend at Mountain Creek Resort in Vernon NJ offering Sprint, Super, Beast and Ultra distances plus a Kids Race and spectator access.

A women only trail race at Lake Mohegan in Fairfield CT offering 5K, 10K and a 4 hour loop option. The event features finisher medals, podium awards, post race food and supports a local non profit.

Two trail events, 25K (about 17 miles) and 10 miles, on technical singletrack and crushed gravel around the Shawangunk Ridge near Ellenville NY. Routes feature steep climbs, two aid stations, a six hour cutoff and a 150 runner cap.

Squatchywaska Mountainfest in the Shawangunk Ridge on April 24, 2027 features a technical 25K and a 10 mile lollipop course with steep climbs, rocky singletrack, two aid stations, and a six hour cutoff.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.