August Wilson once suggested that African Americans leaving the US South during the Great Migration was one of the worst things that happened to the community. Because the Great Migration and the chronicle of African and African American migrants’ histories/herstories are intertwined discussions, this chapter suggests that the American Century Cycle enables Wilson to design a culturally specific study of the affects and effects of the migration on the characters and geographic spaces he plots. It considers how Wilson uses the plays in the cycle to demonstrate his point while also providing hope that, even within the urban North, the realities of the South and transformation of Southern mores will not be forgotten or ignored.