For the majority of people in the early modern Ottoman Empire, pilgrimage was one of the few acts that spurred them to undertake arduous journeys. The city of Damascus often served as these pilgrims' embarkation point from which they set out to not only complete the Hajj in Mecca and Medina but also to visit the graves of the saints and prophets. While the original pilgrimage itineraries and their literary representations were established in the twelfth to fourteenth centuries, a new group of travelers revisited this pilgrimage in the late seventeenth century. Their purpose was to re-witness one of the foundational elements in Islam—the reality of the prophets, saints, and ancients (the salaf)—and to understand how the graves of these men and women became attached to certain locations. This paper examines how pilgrimage inscribed meaning onto Damascus and its environs. It utilizes the travelogues of late seventeenth-century Ottoman intellectuals, in particular, Abd al-Ghani al-Nabulusi and Nabi, along with other material such as sermon collections, restoration orders, and more to understand how pilgrims, their patrons, and their enemies crafted the image of Damascus. The paper adumbrates how in the seventeenth century the two types of pilgrimages—to the Haramayn and to the saintly shrines—became increasingly unified as the importance of prophetic shrines grew. In the process, novel notions of witnessing and visualizing emerged to attach renewed sanctity and meaning to the city through its graves and holy men. More broadly, the paper aims to increase our understanding of pilgrimage and travel in both the Ottoman and larger world and shed light on the challenges that a traditional Islam defined by saints and holy men faced in the seventeenth century.