Great Barrington
Trail Running Calendar near Great Barrington 2026-2027
Explore the top trail runs near Great Barrington for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A timed six hour loop event on Aug 22, 2026 at Jug End State Reservation in Egremont MA with repeated 4.2 mile laps and a 0.75 mile final loop.
September 2026
Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.
September 12, 2026 trail races in Pittsfield State Forest offering 50K, 25K, 15K and a new 5 mile option with proceeds supporting Free to Run.
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.
October 2026
Experience an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.
A 15-mile trail event at Mohawk Mountain Ski Area in Cornwall, CT with 7,140 feet of elevation and a 12-hour limit; participants may run, hike, walk, or compete in a relay, with registration listed as free for the stated window.
Trail running at Mohawk Mountain Ski Area with 5K, 10K, half and marathon routes on ski slopes and state forest, cupless aid stations and finisher medals.
A 5K race at Veeder Tree Farm in Earlton, NY on October 11, 2026, with proceeds benefiting the Leukemia and Lymphoma Society.