Trail Running calendar near Woodbury 2026-2027

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026 with 50K, 25K and a 5.5 mile option, multiple aid stations, a post race meal and proceeds supporting park conservation.

A mountain trail event at Belleayre Resort offering a 25K (~16 miles, 5000+ ft) and an 8K on ski slopes, open to runners and hikers, with carbon offsets, fundraising for The Catskill Center, and pre-race activities.

Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont, MA features a 4.2 mile loop through woods, fields and an apple orchard. Participants run as many 4.2 mile laps as they choose within six hours and receive award..

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 looped trail race in Forest Park, Queens on August 29, 2026. Runners complete twelve 2.5 mile laps on the Orange Trail with about 300 ft of climb per lap and an 8 hour cutoff.

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.

Kingwood Ultras uses a two-mile loop at Horseshoe Bend Park near Frenchtown, NJ, with a central Base Camp, frequent aid, night markings, and handmade wooden finisher awards across multiple timed and distance options.

A family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

A trail race along the scenic Shawangunk Ridge near Rosendale NY offering 70-mile, 30-mile, and half marathon divisions on an unsupported, checkpointed route with shuttle access and event swag.

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.

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 timed trail festival in Pawling, NY offering 24, 12 (day and night), 6 and 3 hour events on a roughly 1.7 mile loop with about 160 feet of gain per loop. The event includes an athlete tent area, aid station offerings, cupless rules, and f..

A three-day trail festival at Wawayanda State Park with events from a 1 mile kids race to a 100 mile race with a 36 hour cutoff, varied terrain, on-course aid support, free weekend camping and a program of panels and a film screening.

A trail event at Nyack Beach State Park offering a 50 mile ultra with about 9,700 feet of ascent and a 27 mile mountain marathon with about 4,900 feet, on looped singletrack with river views.

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.

A 26 mile point to point trail race in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain. Multiple aid stations, post race refreshments, and proceeds support Run Wild, Inc.