Pittsfield
Trail Running Calendar near Pittsfield 2026-2027
Explore the top trail runs near Pittsfield for 2026-2027! We've gathered 6 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.
A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.