This dissertation, “Continental Crossings: The Construction of Europe as a Borderland in Late–Medieval and Early Modern Rhetorics,” considers how a range of late–medieval multilingual authors, writing in English, Latin, French and Dutch, reconceptualised the European literary landscape as an imagined unity—one whose colonial empire they fitfully but consistently supported. Paradoxically, this meant a variety of historical, linguistic, generic, and socio-political propositions, responding to the distinct positions of these major, and often interconnected, figures and texts which found readerships into the early modern period: Giovanni Boccaccio, Geoffrey Chaucer, John Gower, Dirc Potter and the author of the anonymous Middle Dutch Dietsche doctrinale. As participants in the European networks of trade, administration, cultures and languages, I propose that these writers and texts in particular—all connected to major patrons—were crucial contributors to the period’s constructions of Europe’s inner and outer cultural borders, helping to define what it meant to be European and who were restricted from being European. My dissertation closes with a discussion of archival material on the Two Row Wampum Treaty (Guswenta). In making this transatlantic connection, I assess the cross-temporal rhetorical relation between late-medieval constructions of European borders and how the Two Row challenges the border rhetoric used to underpin early modern imperialisms and colonialisms.