Trail Running calendar near Poughkeepsie 2026-2027

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

Point to point 26 miler in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain and multiple aid stations; proceeds support land conservation.

A 50K and 25K trail event on the McDade Trail in Milford PA, out and back along the Delaware River with three aid stations and a cupless course.

A 5th annual 3.1-mile run and 1.1-mile walk at The Church of St. Andrew in Staten Island, and the first leg of the Staten Island FALL TRIFECTA.

Technical trail races in Burlington CT on the Tunxis Trail offering 8K and 5K courses that pass the CT State Trout Hatchery and Nassahegan State Forest.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

A six-hour run and relay at Belmont Lake State Park honoring Fred von der Heydt with individual and team competition on a 1.50 mile loop and commemorative apparel.

A scenic 3.1-mile road and trail run through the New York Botanical Garden, featuring forest and garden views, post-run festivities, and an included All-Garden Pass.

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 an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

Test your limits on a flat one mile loop at the Sussex County Fairgrounds. Choose from 6 to 72 hour timed races or certified marathon and 50K distances with full kitchen and shower access.

A 24 hour Backyard Ultra trail event at Mohawk Mountain Ski Area in Cornwall, CT, featuring about 14,400' of elevation and options to run, hike or walk.

A 30-hour trail ultra at Roosevelt Forest in Stratford CT with 2.5-mile loops, buckles at 100 miles, and a 50 participant field limit.

Timed endurance event in Cohoes, NY on Oct 3, 2026 with 1 hour, 3 hour and 6 hour solo and relay options supporting Flutters of Hope.

Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.

A 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support 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.