The Polish ambassador to the Crimean khan Marcin Broniewski was the first to inform of the “ancient town and castle” located in the vicinity of Mangup and the settlement of Cherkes-Kermen: he visited the site in 1578. The historical name of the town remains obscure. Travelogues often call the ruins of the nameless town the “Circassian castle,” or Cherkes-Kermen after the name of the nearby village. In the late nineteenth century, the site received the common name of Eski-Kermen (Crimean Tatar for the “old castle”), which was used by the locals already in the eighteenth century. In the last decades of the eighteenth and nineteenth centuries, the picturesque ruins of the cave town were popular among the travellers, whose accounts contained myths and legends about the ancient place along with valuable information on the condition of the site and particular objects in its territory. The archaeological excavations in 1928–1934, 1936–1937, and 1978–1982 uncovered the remains of fortifications, sacral complexes, urban buildings, and cemetery allowing the one to infer that there was a typical provincial Byzantine town in the Middle Ages. The archaeological researches in recent decades considerably expanded the notion of the layout of the town. This paper analyses all the currently available data on the topography of the town. Taking the recent years excavations into account, the topography of the town has been reconstructed by different stages, from the Early Byzantine (late sixth and seventh centuries) to the Golden Horde periods (fourteenth century).