At the turn of the twentieth century, the United States Midwest stood poised to lead the nation economically, politically, and ideologically. Its literary productions of this time open upon a landscape of seemingly endless possibilities and expansive futures. My project studies the ideological constitution of these possibilities, finding that they arise from the condition of unprecedented secularity which marked early twentieth-century U.S. modernity. I employ Charles Taylor’s definition of secularization as the shift to belief as possibility rather than assumption, in which new options for belief or unbelief expand like a spiritual nova. This definition makes visible in Midwest texts the different attempts protagonists make to achieve authenticity in a secular age that offers new options for living meaningfully. Like windows onto a figurative landscape, different texts reveal unique vantages as well as startling parallels. I examine the following text grouping, which underscores the heterogeneity of the Midwest: O. E. Rolvaag’s Giants in the Earth, Oscar Micheaux’s The Homesteader, Willa Cather’s My Antonia, Sinclair Lewis’s Main Street, and Black Elk and John Neihardt’s Black Elk Speaks. As rural texts, they collaboratively depict the rural Midwest as a region that is both heartland and subaltern, at once the center of the nation but also estranged from supposed loci of modernity. I argue that their peculiar searches for authenticity offer insight on modern selfhood in a secular age, which constitutes the meaning of the Midwest then and now.