Trail Running calendar near Poughkeepsie 2026-2027

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 trail race in Forest Park Queens featuring 12 laps of a 2.5 mile loop with about 300 feet of climb per lap and a published 8 hour cutoff.

A USATF-NJ Open and Masters cross country championship over a 5K course at Natirar Park in Peapack Gladstone on August 30, 2026. Registration opens July 1, entry is $40 with a $5 USATF-NJ discount and no day of registration.

An outdoor day at Masker's Barn in Feltville combining self guided trail routes, a Trail Treasure Chase, and a five hour Barn party with BBQ, drinks, games, crafts and music.

Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.

An obstacle based 5K at Short Beach Stratford with 18 plus obstacles, family friendly rules, and proceeds benefiting the Sterling Community Center.

Trail races of 70 mile, 30 mile and half marathon distances along the rugged, largely unsupported Shawangunk Ridge near Rosendale NY.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, 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 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.

Pittsfield State Forest trail races on September 12, 2026 offering 50k, 25k, 15k and a new 5 mile option on a double-loop course with three aid stations.

Trail race in Macedonia Brook State Park, Kent CT offering 12K, 25K and 50K loop courses with significant elevation, aid stations, and a cupless policy.

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

Timed trail races in Pawling NY offering 24, 12, 6 and 3 hour options on an approximately 1.68 mile loop with on course aid and athlete camping.

A multi-day trail running festival in Ringwood State Park offering events from a 1 mile kids race to a 100 mile ultramarathon and community support programs.

A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.

A community trail run and walk on September 19, 2026 at Huyck Preserve offering 2, 5, and 8 mile routes through lake, historic track, and waterfalls, with proceeds shared by the Huyck Preserve and Rensselaerville Library.

A community 5K run and a children’s 1 mile fun run at Schodack Town Park on September 19, 2026, raising funds for Hope House. Entry fees include 5K $30 and children free with parents running $30.

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.