Windsor
Walking Events Calendar near Windsor 2026-2027
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Explore the top walking events near Windsor for 2026-2027! We've gathered 35 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
Walkers can take part in a 5K walk starting at 4107 Main Street in Palmer, MA alongside the 5K run. The event supports Palmer High School students traveling to Washington, D.C., and the first 200 registrants receive a T shirt.
Walkers can join the Monster Mile walk; all events start and finish at St. Paul Catholic High School, 1001 Stafford Ave, with free parking via the Maltby Street entrance. Longer courses run through northeast Bristol with a climb at mile 1, roller..
Walkers follow the 5K course of 3.1 Miles starting at Andover Elementary School, 35 School Rd, Andover CT, on a community route alongside the running race. Event includes bib pick up and a Halloween costume contest, with proceeds supporting local..
Walkers take the 4K course from Jimmy Lee Stadium at Crosby High School, on a challenging up, down and flat route around the track and grounds. Parking is in the lots right of the Rotella Magnet School entrance across from the track and packet pick..
The event offers a Halloween themed 1 mile fitness walk through the picture perfect Farmington River Valley with views of Simsbury and the Farmington River. It welcomes walkers of all abilities and includes fitness activities, healthy snacks, giv..
Walkers follow a 5K route on the Collinsville rails to trails bike path, starting near the Crown and Hammer at the Collinsville Bike Path walking bridge by Town Hall with a halfway turnaround. Strollers are permitted and no wheels like bicycles o..
November 2026
Walkers follow the hilly half marathon route in a timed 4 Miles loop starting at American Legion Post 27 in Litchfield. The walk is timed, uses the same course as the races and includes runner amenities and a finish beer.
Walkers can choose a 1 mile walk or join the 5K course starting at Norton School in Cheshire, CT, following the scenic Farmington Canal Line past historic homes. Walkers are not timed; first 550 5K or walk entrants get a long sleeve tech shir..
March 2027
Walkers can join a 2 mile walk starting on Maple Street immediately after the runners depart; the course goes out to the first mile marker, circles back onto Maple Street and finishes at Dwight and Maple. Entertainment on course and a race T shir..
May 2027