This dissertation is the first systematic study of medieval English literary representations of ruins. The limited scholarship on this subject has until now read medieval depictions of ruins as verifying first-hand accounts of the distant past, thus implying that medieval writers saw the material world is a legible source of historical information. However, this dissertation demonstrates that literary representations of ruins in medieval historical literature are most often drawn from earlier literary sources. This reliance upon the written word conveys a debt to what writers read, not what they saw. Ultimately, I argue that medieval literary depiction of ruin serves as a literary device to highlight the importance of the written word in the transmission of history. In the face of the crumbling monuments around them, authors looked to literature to preserve their historical memory. The introduction lays out the scholarship on literary representation of ruins, and examines why a full-length study of medieval representation of the ruins of antiquity has not appeared until now. The first chapter examines literary representations of ruins around the time of King Alfred, focusing on the Old English Orosius and its translation of ruin from late antique Rome to Anglo-Saxon England. The second chapter looks at the Passio Sancti Albani (c. 1167) and its use of classical allusion in its denial of the material ruin as a site of historical knowledge. The third chapter examines the early-thirteenth-century Narracio de mirabilibus urbis Romae, until now considered to be a proto-humanist guidebook to Roman antiquities, and demonstrates how the text quotes Lucan and Hildebert of Lavardin to trouble the notion that the physical world offers an unmediated experience of the past. The fourth chapter turns to Ranulph Higden’s Polychronicon and the alliterative poem St. Erkenwald to show how fourteenth-century writers appealed to literature, not the material object, to know and represent the past. Finally, the coda looks beyond the Middle Ages to the ways in which the Early Modern English antiquaries Matthew Parker and John Leland betrayed their debt to medieval conceptions of historical narrative.