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Walking Events Calendar near Highland Park 2026-2027

Monthly updates for Highland Park

Get new running races (and updates) in your inbox every month.

Explore the top walking events near Highland Park for 2026-2027! We've gathered 126 great walks in the area. Check out our detailed list below to find your next local walk.

March 2027
The event offers a 2 Mile walk alongside the running races, starting and finishing in Grant Park and weaving through Chicago's Loop; an Adaptive Program supports participants with impairments.
April 2027
Routes of 10 Mile and 5K start at Montrose Beach on the Chicago lakefront, featuring a climb over Cricket Hill and a Wilson track finish. Walkers are encouraged to register for the 5K.
May 2027
Walkers can take part in the 5K walk or the 1 Mile fun walk at Cantigny Park in Wheaton, with the 10K held alongside the walking options. Walkers are asked to line up behind runners at the start and stay to the side on course to keep the..
Walkers can choose a 5K or 1 mile course in Northbrook starting at 2370 Shermer Rd, offered alongside the running races.
June 2027
Walkers follow a 5K USATF certified loop through Deer Grove Forest Preserve starting at Picnic Grove #2 in Palatine. Water stations are on course, parking is very close and light food and drinks await at the finish, no gear check.
Walkers can join the scenic 2K Fun Walk from 300 N Grove Ave along the Fox River Trail; the untimed walk includes an entry bib, event tee shirt and team and family discounts.
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