Through examining the common themes in the writings of five anarchist women writers, I argue their writings are representative of ideological regionalism, or the convergence of factors that give rise to a political ideology that is then expounded through the literary production of a particular time and place. I analyze the economic, sexual, and “religious” politics across fiction, non-fiction, and poetry, connecting arguments about class, individualism, feminism, and anarchism to a foundation of Midwestern cultural ideology. Ultimately, I argue that economic, political, and historical conditions promulgated an exceptionalist American anarchism rooted in settler anti-statism.