From a contemporary perspective, Wisconsin hardly counts as part of any possible “German-speaking world,” but a century ago, there were very real and robust German-speaking communities in much of Wisconsin and in other parts of the surrounding Upper Midwest. This was true to the point that the major history of the state includes the statement that Wisconsin was “a society made up of separate societies, each with its own churches and other organizations, its own customs, and even its own language” (Thompson 1973–1998: vol. 2, 128). This was true for Norwegian and Polish and other languages, but nowhere more true, nor true on a larger scale, than among German speakers. Today’s Wisconsin is majority English speaking – emphatically not German speaking – yet the English of the state and the state’s literal and figurative landscape still show clear marks of this linguistic history. In this chapter, we take that earlier status and trace key developments along several dimensions.