Trail Running calendar near Mount Kisco 2026-2027

A six-hour loop ultra at Jug End State Reservation in Egremont, MA featuring a 4.2 mile course through woods, fields and an apple orchard. Age-group awards and a handmade finisher mug; proceeds benefit 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 trail ultramarathon in Forest Park, Queens. The race is 12 laps of a 2.5 mile counterclockwise loop with about 300 ft climb per lap, aid stations after each lap, and an eight 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.

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

A trail event in Rosendale, NY featuring 70 mile, 30 mile and half marathon divisions along the Shawangunk Ridge. The course covers varied terrain, is unsupported, and uses shuttle transport and checkpoint controls.

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 group run along the Farmington Canal Heritage Trail covering about 56 miles from West Suffield to New Haven. It is a fundraiser for Mental Health Connecticut and requires self support with a 14 hour time limit.

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.

A timed trail festival at Lakeside Park in Pawling offering 24, 12, 6 and 3 hour events on an approximately 1.68 mile mixed surface loop with aid station items, a cupless policy, and finisher medals.

A weekend trail festival in Ringwood State Park featuring a 100 mile race with a 36 hour cutoff, multiple shorter distances, Friday panels and film screening, free camping, and nonprofit partnerships supporting mental health.

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 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.

A rugged trail marathon in Shandaken, NY with a point to point course through the Slide Mountain Wilderness and nearly 7,000 feet of vertical gain. Proceeds support Run Wild, Inc.

Trail ultramarathon in Milford, PA offering 50K and 25K courses along the McDade Trail beside the Delaware River. The mostly flat, non technical route has three aid stations and is a cupless event.