The present essay focuses on Caravaggio’s ‘Madonna di Loreto or Madonna dei Pelegrini’ and its unique representation. In this painting, Caravaggio depicted an encounter between two pilgrims and the Madonna with the baby Jesus. At first glance, the importance of Loreto and the miraculous voyage of the Madonna’s house from Nazareth to Loreto is unrecognizable in the painting. The historical dimension of the miracle, so prominently displayed in earlier representations of the Loreto story is absent. Yet, Caravaggio’s choice of representation still marks its presence by adding a cluster of bricks revealed where the plaster has cracked and fallen away beyond the doorpost. These stone bricks, as I would like to argue, may help us locate additional meaning in the painting. The bricks connect two worlds, that of the Madonna and child in Nazareth and that of the two pilgrims in Loreto. Caravaggio created a superposition of two locations and two times with the help of a common wall. The integration of both moments in time and place defuses the historical character of the scene. The unhistorical perception yet replicated authority of the location depicted, enhances the importance and significance of the scene within the site. This will be argued with the help of pilgrims’ travelogues to both locations.