Highland Park has one of the most walkable suburban downtowns accessible by Metra train. Back in March, I had a day off and hopped on the Union Pacific North to check it out. If offers a pleasant downtown, great neighborhoods to stroll, some nice lakefront parks, a beach and outdoor concerts at Ravinia.

If you're looking for a nice bike ride from Chicago, you can also ride up the North Branch Trail to Highland Park, or the Green Bay Trail provides a bicycle connection through the other north shore suburbs north from Wilmette.