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This essay considers the integral role that Piers Plowman played within American colonial settlement and westward expansion and how that history has influenced the authors’ pedagogy in literature and visual design classes, respectively. Beginning with its earliest-known American reader — Thomas Dudley, governor of the Massachusetts Bay Company — Piers Plowman appeared regularly in the libraries, letters, and speeches of consequential figures in American law and land use, including Thomas Jefferson and Theodore Roosevelt. By tracing the allegory of the Plowing of the Half-Acre from colonial New England to twentieth-century California, the essay demonstrates how Langland’s agricultural metaphorics of collective obligation and individual conscience embedded themselves deeply within not just English but American histories of land management and social improvement. This background has inspired new teaching initiatives for both authors, including an environmental humanities partnership between CSU Monterey Bay students and The Huntington Library, Art Museum, and Botanical Gardens.