Cycling & running events in Pittsfield, 2026

Pittsfield Base Miles

Running: Locals run downtown, Clapp Park, Canoe Meadows Wildlife Sanctuary, and Pittsfield State Forest when the legs want dirt. 5 to 5 miles by pace group. The route covers 42 km and gains 182 m, so it works for steady base miles. The Ashuwillticook Rail Trail runs 73 km and gains 40 m. Tails & Trails State Forest Run, Notchview Ultra, and Sweltering Summer Ultra sit on the local anchor race list.

Cycling: Locals ride the Ashuwillticook Rail Trail for clean Z2 and go west or south when the climbing itch shows up. Berkshire Bike Path Council keeps the path talk alive, and Berkshire County has a real bike community. Kennedy Park Loop runs 4 mi when you want rougher work. 7%. Mount Greylock Hill Climb Time Trial, Berkshire 40- Race Day XCM, JAM Fund Grand Fundo, and Farmer’s Daughter Gravel Grinder are the anchor events.

Season: Summer is the best block here, with warm, pleasant days and enough daylight for intervals after work or long Z2 before dinner. Locals use Clapp Park, downtown Pittsfield, and Pittsfield State Forest when the air feels good and the legs need routine. The city sits at 1,039 ft (317 m), so winter changes the whole setup fast. Runners keep grinding when the paths are slick, and cyclists shift toward fat biking at Pittsfield State Forest, Kennedy Park, Mount Greylock, and Greylock Glen when the snow makes the road bike feel pointless.