Trail Running calendar near Stamford 2026-2027

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K and a 5.5-mile option across mixed dirt roads and single track. On-course aid and post-race meal included; proceeds support park conservation.

A timed six hour ultramarathon on a 4.2 mile loop at Jug End State Reservation in Egremont, MA. The wooded course includes fields and an apple orchard and benefits the Louison House.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A 50K in Forest Park Queens run as 12 laps of a 2.5 mile Orange Trail loop, each lap adding about 300 feet of climb and with aid stations after every circuit. The event combines a grassroots race atmosphere with an 8 hour cutoff.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A trail event on the Shawangunk Ridge near Rosendale offering 70 mile, 30 mile, and half marathon divisions over rugged, minimally supported terrain with shuttle logistics and enforced checkpoints.

An urban obstacle race on the Jersey City waterfront on September 12, 2026. The event features a fast 3 mile course with 20 plus city-style obstacles, chip timing, new finisher medals, awards, and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

A group run along the Farmington Canal Heritage Trail covering roughly 56 miles from West Suffield to New Haven, held as a fundraiser for Mental Health Connecticut. The event is largely self supported with basic volunteer aid stations and a..

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

A multi-race trail festival at Lakeside Park in Pawling, NY offering timed 24, 12 day, 12 night, 6 and 3 hour events on an about 1.68 mile loop with on-course aid, music, and finisher medals.

A weekend trail festival at Wawayanda State Park offering races from a 1 mile kids run to a supported 100 mile event with a 36 hour cutoff, camping, panels, aid stations and nonprofit partnerships for community support.

A USATF sanctioned trail ultra near Upper Nyack, NY offering a 50 mile race with about 9,700 feet of gain and a 27 mile mountain marathon. The course uses a 4 mile out and back plus repeated 11.5 mile loops along the Palisades ridge and Hud..

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

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.

Out-and-back 50K and 25K on the McDade Trail near Milford, PA, on rail-trail cinder and some singletrack. Three aid stations, a cupless course, and a poker-chip turnaround for the 50K.