Can a place, or its representation, ever be timeless? The Monastery of Saint Catherine at Mount Sinai is the oldest, continuously existing Eastern Orthodox community in the world. It has celebrated the Byzantine liturgy uninterrupted for centuries while the Sinai fathers have maintained their pursuit of prayer and solitude in the desert. For scholars and art historians, the monastery is justly famous for its ancient library and unrivalled collection of icons. The notion of timelessness has been asserted in the literature and scholarship on Sinai’s history, as well as in the monastery’s intentional construction of religious identity and its self-representation through visual, architectural, and material means. The accessibility of the past in the present is the central claim made by pilgrimage art. Paradoxically, it is through close examination of the experience and production of sacred place and visual identity at Sinai that we gain a better understanding of the changes and innovations actually necessary for the monastery’s survival.,Chapter 1 of this dissertation begins with the formulation of a topographical landscape view representing Mount Sinai and the Monastery of Saint Catherine at the end of the sixteenth century. This image circulated in the form of painted devotional panels, usually part of a triptych, and in prints illustrating accounts of pilgrimage and travel in the Near East. Dependent upon Renaissance pictorial conventions and the developments of Early Modern cartography, the topographical landscape also incorporated earlier religious imagery depicting Sinai’s sacred past. The combination of these visual modes created a new loca sancta image for the pilgrimage site that could reach multiple audiences and, by offering pictorial access to important figures and events from the monastery’s history, became an icon of place. Previous scholars have focused on the iconographic origins of these images rather than their function. I argue for the significance of their Early Modern context and, by addressing earlier stages of pilgrimage art at Sinai in reverse chronological sequence, hope to undo our expectations for a logical narrative invested in the forward progression of time. While I have selected case studies (and representative samples) based upon the compositional elements found in the sixteenth-century topographical image, namely the holy figures representing Sinai’s past and the physical landscape with its commemorative topography of chapels and pathways connecting the monastery’s loca sancta, each of the subsequent chapters also investigates a period of significant disruption (political, social, even religious in nature) for the monastery and the creative refashioning of its identity through visual and material means.,Chapters 2, 3, and 4 analyze the roles of three primary patron saints – Moses, St. Catherine of Alexandria, and the Virgin of the Burning Bush – at the Sinai monastery between the eleventh and thirteenth centuries, especially as depicted in the monastery’s corpus of Middle Byzantine and Crusader icons. Images of Moses before the Burning Bush and receiving the Tablets of the Law drew upon the program of sixth-century mosaics covering eastern wall of the monastery church. Like the mosaic scenes, these icon panels defined holy ground at Sinai in relation to theophanic vision; Moses remained the primary model for pilgrimage and for the experience of divine revelation. Although the monastery now bears her name, the cult of St. Catherine was only introduced at Sinai sometime between the eleventh and thirteenth centuries. The availability of her relics in the monastery church may have reflected the demands and devotional interest of an increasing number of Latin pilgrims during and after the Crusades. However, the monastic community quickly assimilated Catherine’s tomb within its liturgical space and pilgrimage rituals, as well as adapting the veneration of her icon within a larger body of specifically Sinaitic saints. Representation of Mary as the Virgin of the Burning Bush (ἡ τῆς βάτου) appeared at Sinai for the first time during this same period. Identified through the conflation of Mary’s figure with the Burning Bush of Moses’ theophany or by accompanying inscription, this new iconography gave visual form to the longstanding typological association between the Mother of God and Moses’ vision, which was interpreted as a prefiguration of the Incarnation. Icons of the Virgin ἡ τῆς βάτου frequently place Mary at the center of a Deesis-like composition, emphasizing the importance of her intercessory role on behalf of the monastery and pilgrimage site. They also present this new Marian image as a fulfillment of Old Testament events at Sinai, a manifestation of divine presence now made available through the icon.,Chapter 5 turns to the physical landscape and commemorative topography established at Sinai between the fourth and sixth centuries, when the church and monastery walls were built by Emperor Justinian I (r. 527-65). In this concluding chapter, the materiality of rock and stone provides the interpretive matrix for identifying Sinai’s holy places. Commemorative chapels, physical landmarks, and connecting pathways were all means of shaping the surrounding desert terrain to match an authorizing scriptural narrative. Place could also serve as icon. Natural phenomena, such as dendritic patterns in the red granite at Sinai, were collected as relics and imprints of the Burning Bush. Pilgrims added their names and prayers to the Nabataean inscriptions that they read as examples of ancient Hebrew, mapping out the desert routes of the Israelites’ journey in relation to their own. It is the physical landscape that finally anchors the experience of sacred place at Sinai, allowing past and present to coexist and reshaping each, even as it offers the illusion of permanence. We continue to write human history over the skin of the earth and create new topographies of meaning – a process to which this study contributes.