Focusing on transborder travel narratives by two German authors and one Polish author, “Cold War Crossings” investigates how their writing responds to the postwar demarcation of separate Eastern and Western spheres of influences. Central to each of their oeuvres is the topos of the border broadly conceived, from the material, ideological, and psychic boundaries of the Iron Curtain to the Saussurean bar of the linguistic sign. By presenting border-crossing as an act of both political and aesthetic transgression, these writers advance uniquely literary alternatives to the rigid geopolitical divisions of their age. This dissertation analyzes the way in which each author’s poetics of the border informs, among other things, their manipulation of narrative structure, their unique employment of figurative language, and their shared proclivity for intertextuality, all of which address and reorient different kinds of textual boundaries. In this way, it is a contribution to the ever-expanding field of border studies and other scholarly investigations of the discursive production of mental maps. At the same time, however, the dissertation argues by way of its three case studies for a closer examination of the formal elements of literary texts that often go overlooked in such analyses. Conceived as an interdisciplinary and comparative study, “Cold War Crossings” seeks to overstep barriers between national literatures as well as disciplines by combining cultural studies, literary criticism, and historical analysis. Furthermore, the dissertation’s joint study of German and Polish literatures also contributes to recent debates on Europe as it counteracts traditional Eurocentric approaches that disregard Eastern Europe.