Chicago: Downtown & Central

North Shore: Highland Park, Glencoe, Winnetka

There’s wonderful running on Chicago’s north shore, including some lovely parks and residential neighborhoods. One route follows the North Shore Classic Half Marathon course, featuring Chicago’s Highland Park neighborhood. Run on some of classic, tree-lined streets in the area made famous in the movies made by director John Hughes in the 1980s, including “Ferris Bueller’s Day Off,” “Sixteen Candles” and “The Breakfast Club,” to name just a few. The loop follows a counter-clockwise loop tour of the North Shore area, including the Green Bay Trail.

Just south of Highland Park, there’s wonderful neighborhood running in Glencoe and Winnetka, which are two affluent neighborhoods with attractive residential streets.



  • Numerous options, including 13.1 mile Highland Park tour, or DIY route of Winnetka and Glencoe.
  • Wolter’s Field track and field complex at Highland Park High School.