Trail Running calendar near Garrison 2026-2027

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.

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.

An obstacle based 5K at Short Beach in Stratford CT featuring more than 18 obstacles and a family friendly course. Proceeds support the Sterling Community Center including the food pantry and youth programs.

A trail event along the 70-mile Shawangunk Ridge near Rosendale, NY, offering 70-mile, 30-mile, and half-marathon routes across varied terrain. The course is minimally supported and uses shuttles with Rosendale-only parking.

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 charity 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven. The unsupported group event raises funds for Mental Health Connecticut and requires self support and a 14 hour completion limit.

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.

Blue Ridge Winery Wine Run 5k in Saylorsburg PA on September 13, 2026 features a two lap course around Blue Ridge Estate Vineyard and Winery with chip timing by J3 Timing. Entry includes a shirt, collapsible wine glass, medal and a pour of..

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

A timed trail festival in Pawling, New York offering 24 hour, 12 hour day and night, 6 hour and 3 hour races on a short mixed surface loop with aid stations, crew areas, finisher medals, and distance based awards.

A multi-day trail festival in Ringwood New Jersey, mid-September 2026, offering races from a one mile kids event to a 100 mile race with a 36 hour cutoff, free camping, community programming, and nonprofit partnerships.

A loop-based trail event in Upper Nyack with 50 mile and 27 mile options, significant elevation, three aid stations, and a 14 hour cutoff. Parking and nearby overnight accommodations are coordinated with a local retreat center.

Trail run and walk at Huyck Preserve in Rensselaerville NY on Saturday September 19 2026. Routes of 2 5 and 8 miles pass Lake Myosotis and a historic racetrack while raising funds for local organizations.

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.

The Cat's Tail Trail Marathon in Shandaken, NY is a 26 mile point to point trail race through the Slide Mountain Wilderness with about 7,000 feet of vertical gain. The race offers aid stations, post race refreshments, and a 25 percent veter..

Trail ultramarathon in Milford, PA along the McDade Trail offering 50K and 25K out and back courses from Smithfield Beach. The route is mostly flat cinder rail trail with some singletrack, three aid stations, and a cupless policy.

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.