From 1895 to 1938, the Roycroft Shops of East Aurora, New York produced books and craft goods, guided by the William Morris-inspired vision of founder Elbert Hubbard. Roycroft was one of the longest-running and most successful Arts and Crafts communities in the United States, and it continues to be an important landmark in East Aurora today, where both its physical campus and artistic legacy have been preserved. However, while the Roycroft campus has received a great deal of attention for its craft production, cultural influence, and eccentric founding figure, critical aspects of Roycroft’s history have remained relatively understudied in scholarship and in the legal backing for Roycroft’s preservation. This thesis uses prior scholarship, Roycroft publications, and Roycroft archival collections to analyze Roycroft through the lens of labor history, architectural history, and the inextricable relationship between the two. In doing so, this thesis states that the nexus of labor and architectural history informs, expands, and strengthens the arguments for the significance of the Roycroft campus, as a truly distinctive Arts and Crafts community, as an imaginative-but-fraught alternative to the mechanized industrial hegemony of the turn-of-the-century, and as an ongoing dialogue about how individuals and organizations in society react to the ceaseless march of modernity.