Trail Running calendar near Great Barrington 2026-2027

A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarship..

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.

Point-to-point trail runs of 112 or 50 miles along the New England Trail blue blazes to Guilford, CT, requiring dedicated crews, navigation, and night trail experience.

A two distance event at Rockland Lake State Park with a flat, accessible 5K and a rugged 10K up the Long Path to Hook Mountain Summit. The 10K features 1,300 ft of elevation gain and one on course aid station.

A mountain trail event in Roxbury NY on June 6, 2027, featuring a 6.5-mile course with 3500 ft climb and a 5k with steep early ascent and a downhill finish.

Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educat..

A two day Spartan obstacle event at Carter & Stevens Farm near Barre MA featuring Sprint 5 km, Super 10 km and kids races across wooded trails and open pastures.