Pittsfield
Walking Events Calendar near Pittsfield 2026-2027
Monthly updates for Pittsfield
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Explore the top walking events near Pittsfield for 2026-2027! We've gathered 15 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
A 3.1 mile walk or run open to all abilities, held at High Lawn Farm in Lee MA along Laurel Lake. Technical shirts are available to the first 150 registered walkers or runners, and students participate free and get free ice cream at the finish.
August 2026
Clapp Park, 215 West Housatonic St, Pittsfield hosts an 8 hour event on a certified dirt and cinder track looping .355 mile. The event is walker friendly; walkers may do unlimited laps and trackside aid has bottle drop, no contact refills and persona..
The event offers walking options 3K and 8K through downtown Shelburne Falls, MA, starting near 75 Bridge St. Registration is required and there is no at the door registration.
At Jug End State Reservation in Egremont MA walkers follow a 4.2 mile loop through woods and fields. Many laps within 6 hours count but partial laps do not; .75 mile loop opens last hour.
September 2026
Walkers may choose 5k or 1m in Washington Park Albany alongside the running races. Packet and T shirt pickup Saturday 10:00 to 12:00 at American Cancer Society Hope Club, 1 Penny Lane Latham; shirts guaranteed if registered by August 24.
Walkers follow the trail course at Schodack Town Park on a 5K route, with a children's 1 mile fun walk option alongside the races. Entry is $30 for the 5K and children are free for the 1 mile.
Walkers can choose the 1 mile option or join the 5K route, both based at the Williamstown Youth Center, 66 School Street. Daily and occasional walkers, families with pets and strollers are welcome and on site registration is available.
October 2026
Walkers follow a 5K route starting at Chesterwood, 4 Williamsville Rd, Stockbridge MA, alongside the running races. The event offers refreshments and awards and carries a $35 entry fee.
November 2026
Walkers follow the 5K of 3.1 Miles from the Berkshire Family YMCA at 655 Gage Street in downtown Bennington, with a short loop by the adjacent fenced field. Kids Dash is free on site and packet pickup is offered the night before.
The Turkey Walk is a 1 Mile walk in Troy, NY, held alongside the Troy Turkey Trot road races on Thanksgiving Day. Entry fee ranges from $20 to $25 depending on registration date.
May 2027
Walkers can choose 5K or 1.5 Mile run/walk routes starting at 5 Bridge St in Haydenville, MA. Proceeds support local veterans and the first 100 registrants receive an official race T shirt.