In the decades around the turn of the twentieth century in which the writer, literary theorist, and activist Hamlin Garland lived in Chicago, he made great efforts to make the city the center of American literature. While later readers categorized his work simply as Midwest regionalism, Garland believed that regionalist literatures constituted global avant-gardes and that developing regional literary centers would lead to a transformation of literary value. This chapter surveys Garland’s work across thirty years, examining his theory of literary localism, his investment in developing the Chicago literary and artistic world, his changing vision of the American West, and his deflected relationship to early American modernism. In addition to his most famous writings, Main-Travelled Roads and Crumbling Idols, the chapter discusses less well-known works including The Land of the Straddle-Bug, Rose of Dutcher’s Coolly, his writings on Alaskan mining and Native American reservations, and his biography of U. S. Grant. It also explores his affiliations with Chicago personalities including Henry Blake Fuller, Harriet Monroe, and the influential Chicago magazines the Chap-Book and Poetry.