Set against the scholarly and historical backdrop of 18th- and 19th-century Germanphilhellenism, this dissertation examines how the idea of ancient Rome – the city, its history, and its literature – shapes ideas of history in the writings of Johann Wolfgang von Goethe, Wilhelm von Humboldt, and Immanuel Kant. The idealization of ancient Greece looms large in both the writings of this period in Germany and in scholarship written about them This cultural obsession also coincided with and colored new theories of history and education that emerged in this intellectual milieu. As a result, moments in which these thinkers and theorists address Rome, especially outside specialized discourses of classics and ancient history, are rare and frequently offer unfavorable contrasts with Greece – or have at least been interpreted as doing so. Contributing to a scholarly counternarrative to the dominance of philhellenism, I adopt a methodology of sustained literary close reading and comparative study of Latin, Greek, and German texts to excavate the presence and influence of Rome in the works of these prominent contributors to early historical thought. The following chapters comprise three discrete case studies of such Roman moments: first, in the aesthetic discourse of Goethe’s Italienische Reise; then in the theoretical essays and elegiac poetry of Wilhelm von Humboldt; and finally in natural metaphors of Kant’s Idee zu einer allgemeinen Geschichte in weltbürgerlicher Absicht. While each of these studies showcases a distinct approach to Rome, its history, and its literature in German thought, together they illustrate Rome’s capacity to serve a tropical or metaphorical role in their language. More specifically, despite these different approaches, ideas of Rome show a persistent affinity for the language and figures of thought these authors use to describe time and history, as perceptions of the enormous scale of both the city and its long history find reflection in their efforts to assign meaning to the manifold phenomena of the past. These studies illustrate how Rome and Roman literature are naturalized and incorporated to German ideas of history around the turn of the 19th century but also thus reveal tensions and contradictions within and across disciplinary boundaries of history, philosophy, and classical studies.