This essay examines David Foster Wallace’s literary representations of the Midwest region. Reading The Broom of the System (1989), “Derivative Sport in Tornado Alley” (1992), and “The View from Mrs. Thompson’s” (2001) in the light of the patently regionalist treatment of landscape in his posthumous work, The Pale King (2011), I trace a consistent and continuous regionalist trajectory through his oeuvre. His work, which is frequently conceived of as a metafictional commentary on postmodern systems of technology and media culture, maintains an urgent preoccupation with mapping and depicting regional landscape. By reading his texts through the lens of regional criticism and within the frameworks of space/place theory and géocritique, I demonstrate the centrality of the Midwestern environment to his texts’ endeavors to restructure the literary cartography of the U.S. In recreating the Midwest on the page, Wallace offers an alternative role for regionalism in postmodern literature and an ethical imperative to locate oneself—both in one’s immediate surroundings and within regional, national, and global networks—via awareness of place. Literary representations of region, this report contends, can serve to ground and to implace the contemporary reader.