Milwaukee
Walking Events Calendar near Milwaukee 2026-2027
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Explore the top walking events near Milwaukee for 2026-2027! We've gathered 59 great walks in the area. Check out our detailed list below to find your next local walk.
October 2026
The event offers walkers a 3.1 Miles 5K Walk from Cupertino Park along the paved Oak Leaf Trail beside Lake Michigan through south shore parks, with lake views and wooded sections. Walkers join runners and ruckers on an organized paved course.
November 2026
Walkers can choose the 3K course starting at W173S7743 Westwood Dr in Muskego, touring historic Pioneer Drive and wide subdivision streets. Walkers are not timed, dogs are allowed on the walking portion, and t shirts are guaranteed for those regist..
The 2 Miles walk in Cedarburg follows local roads near Covered Bridge Rd; walkers park at the church and walk north to the school start line, entering through the school athletic entrance at 1425 Covered Bridge Rd. The course is dog and stroller..
Walkers choose 5K or 8K routes that start and finish at McKinley/Veterans Park on N. Lincoln Memorial Drive. Water stations provide water; course limits are 1 hour 20 minutes and 1 hour 30 minutes respectively; strollers allowed.
December 2026
Walkers will find a dedicated 5K Walk of 3.1 Miles, starting at the E.B. Shurts Building, Fox River Sanctuary in Waukesha. The walk takes place alongside the event's running races on the same day.
Walkers can choose a 5K timed route or a 1K kids course at Greenfield Park in West Allis, with park scenery and holiday music. The 5K includes a commemorative mug and warm cocoa for finishers, and a dog friendly option is available for an..
Walkers have an untimed 3K walk starting at 611 West Main Street in Waterford, Wisconsin, for fresh air and Christmas spirit alongside the on site 5K run. The walk is non competitive, includes a virtual walker option, and T Shirt or Beanie orders..
The event offers walkers a 1.75 Miles walking only course at Frame Park in Waukesha on a fast, flat route that winds along the Fox River. The walk runs alongside the running races and other JanBoree winter activities.
February 2027
March 2027
The 5K Walk covers 3.1 Miles and starts at 810 W College Ave in the E.B. Shurts Building, Fox River Sanctuary. Route follows the smooth scenic Glacial Drumlin and Fox River Trails alongside other event races.
April 2027
A relaxed 3K walk at Greenfield Park in Milwaukee on a fast, scenic loop course suitable for all ages. This non competitive, family friendly walk runs alongside the 5K event and includes a long sleeve tech shirt, finisher medal and post event foo..
May 2027
The event includes a 5K run walk in Cedarburg, Wisconsin on a chip timed, fast and certified course. Walkers can use packet pick up at Cedarburg High School or earlier pickup days and will find post race food, music and awards alongside the runni..