This dissertation traces the history of road construction in Ethiopia from the 1850s to 1950s, examining how roads became a central symbol of modern imperial power and altered the ways ordinary people came into contact with the state, and with each other. Most accounts of road construction in Ethiopia start with the Italian occupation from 1936 to 1941, which saw Mussolini realize, at considerable cost to Italy, an expansive network of roads to connect the territories of his new East African empire, Africa Orientale Italiana. While the central chapters of this dissertation, indeed, focus on road projects launched during the five years of Italian Fascist rule, they seek to add to the scholarship in a number of important ways. To begin with, the scale of the “Mussolinian” enterprise has tended to overshadow the fact that Ethiopian emperors had already started to use roads to consolidate and centralize their power decades earlier. Highlighting the continuities between the Ethiopian imperial vision and the later Italian one allows us to re-periodize the story of roads in the making of the modern Ethiopian state, and suggests that there is methodological value in examining the history of an infrastructure over the longue durée. Then, by carefully reading between the lines of a combination of “official” and less conventional Italian sources, including the records of the Italian military tribunals for East Africa and the photography archives of the Istituto agronomico per l’Africa Italiana and the Touring Club Italiano, I show how road construction during the Italian occupation altered the spaces and experiences of daily life for Ethiopians, and how Ethiopian realities, in turn, thwarted and complicated Italian ambitions. As a technology that transformed mobility and expanded the reach of the state, roads created new obligations and opportunities for the communities they traversed. In reconstructing how people perceived and capitalized on this connectivity, this dissertation also speaks to the histories of labor, imperial governance, and urbanization in modern Ethiopia.