Trail Running calendar near Poughkeepsie 2026-2027

A multi-day timed running festival at the Sussex County Fairgrounds with a certified 1-mile loop, options from 6 to 144 hours plus Marathon and 50K, night lighting, central aid station, camping and electronic lap timing.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A 5K run/walk through Bethpage State Park featuring soft trails, live timing, free finish-line photos, and advance bib pickup at Orangetheory Fitness Farmingdale.

A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

A trail 5K at Blydenburgh County Park in Hauppauge with on site refreshments, an in person and a virtual participation option, and proceeds benefiting the Never Stop Running Foundation.

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.

Obstacle course races at Bethel Woods in June 2027, featuring Sprint, Super and kids races, team entries, spectator options, and variable course conditions.

Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.

A two distance event at Rockland Lake State Park with a flat, accessible 5K and a rugged 10K up the Long Path to Hook Mountain Summit. The 10K features 1,300 ft of elevation gain and one on course aid station.

A mountain trail event in Roxbury NY on June 6, 2027, featuring a 6.5-mile course with 3500 ft climb and a 5k with steep early ascent and a downhill finish.

Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educat..