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Walking Events Calendar near Winchester 2026-2027

Monthly updates for Winchester

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Explore the top walking events near Winchester for 2026-2027! We've gathered 42 great walks in the area. Check out our detailed list below to find your next local walk.

December 2026
Dec
12
Sa

St. Nicholasville Ugly Sweater 3K

Road Race Walk 3 km
Walkers may take the 3K paved course that starts at the Coolidge Building and ends at the Courthouse; strollers and dogs on fixed length leashes are allowed. The course is chip timed and a virtual 3.1 Miles run/walk option is available.
April 2027
Apr
17
Sa

Brandon True Memorial Heroes For The Homeless 5K

Road Race Walk 5 km
Walkers may choose a chip timed 3.1 Miles run/walk on flat paved trails or an untimed 1 Miles fun walk starting at Coldstream Park/Legacy Trail. Walkers, strollers and dogs on a fixed length leash are welcomed.
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