For some attractive residential neighborhood running in Milwaukee, we recommend Whitefish Bay and Fox Point. These adjacent neighborhoods are a few miles north of downtown, and sit on Lake Michigan.
Whitefish Bay is laid out in the style of a classic older neighborhood, with tree-shaded streets, attractive homes, sidewalks, and period lamps. Create your own route north of Shorewood Rd., between the Milwaukee River Greenway/Lincoln Park and the Lake. There are some National Register listed homes in this neighborhood. You can also continue north past Cardinal Stitch University to the Fox Point neighborhood, which also has some nice streets for running.
Add-On: The Milwaukee River Greenway/Lincoln Park are just west of the neighborhood.