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 9 great walks in the area. Check out our detailed list below to find your next local walk.
August 2026
The Last Mile features a 1 mile or 2 mile walk on Friday alongside a timed 5K. Mapped walk routes are provided and registrants by July 1 receive a free t shirt.
September 2026
Walkers use a measured 5K through downtown Northfield or a 1 Mile kids loop with mile markers and a midpoint water station. The 5K starts on Rt 12 by Northfield Savings Bank; strollers headphones and dogs are not allowed.
Walkers can take part in the 5K road walk starting at Ludlow Community Center, 37 Main St, Ludlow VT, alongside the running races. Pre registration is $25 and the event includes a post race cookout, family friendly activities and department award..
Walkers follow a 3.1 Miles route through historic Orwell, VT, starting at 480 Main Street on gentle town streets suited to a leisurely pace. All in-person participants receive a custom T-shirt and wooden token, and walkers are welcome alongside t..
Walkers can choose timed 1K or 5K courses at 55 Collins Drive in Middlebury, VT. The event runs alongside family friendly activities, food trucks, and a community resource fair, with bib pick up available.
November 2026
March 2027
Walkers may take the 5K or 1 Mile course starting and finishing at Colburn Park in Lebanon along relatively flat residential roads by the scenic Mascoma River. Walkers must start at the rear of the pack and strollers are allowed from the back..
June 2027
Walkers can join a 1 mile fun run/walk starting at Colburn Park, Lebanon NH, with free parking nearby; the event also includes a 4 miles loop along the Northern Rail Trail and Riverside Drive.