Great Barrington
Walking Events Calendar near Great Barrington 2026-2027
Monthly updates for Great Barrington
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Explore the top walking events near Great Barrington for 2026-2027! We've gathered 11 great walks in the area. Check out our detailed list below to find your next local walk.
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..
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 follow a 1.5 mile mixed pavement, field and trail course from Littleville Road to the dam flagpole, with the steep DAM hill; bib pickup at Gateway Regional School lot.
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.
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.
Walkers can choose 5K, 10K, Half Marathon or Marathon at Mohawk Mountain Ski Area on ski mountain and forest trails, with aid stations and cupless policy.
Walkers complete the 5K course via two loops of the Lime Rock Park circuit in Lakeville CT. The venue provides public restrooms and a water station at start and finish, and wheelchairs and disabled push strollers are welcomed.
Walkers can take the 5K route through scenic Cornwall Green and the Cornwall Valley alongside runners and their dogs. Family friendly activities, live music and food accompany the event and proceeds benefit the Little Guild animal rescue.
Walkers can choose the 5K course that starts and ends at Hudson High School and follows a USATF certified route through residential streets, while a free kids 1 mile borders the Hudson Fireman's Home and Museum. Entry is free for those 17 and..
November 2026
A 5K walk starts on West St at Berkshire Community College, loops through the BCC campus and Meadowridge to finish in Paterson lot; porta potties and water at miles 1 and 2.