Bennington
Walking Events Calendar near Bennington 2026-2027
Monthly updates for Bennington
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Explore the top walking events near Bennington for 2026-2027! We've gathered 11 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Guided uphill hike up Stratton Mountain covering 2.14 Miles from base to summit through scenic mountain terrain, followed by a gondola ride down. Participants meet at the main base area in South Londonderry; moderate effort and advance sign up is..
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..
September 2026
Walkers may enter the half marathon or 5K, starting and finishing at Dana Thompson Recreation Park in Manchester VT, on scenic village and country roads past farmland and fall foliage. The half marathon has a 3.5 hour limit, six staffed water s..
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
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.