The expansion of the Bosporan Kingdom (the interior colonization of Bosporus) was caused by the need for commercial grain in the Greek markets of the Mediterranean. The steep rise in the Bosporan rulers’ incomes followed the annexation of Sindica—one of the most fertile lands of the Northern Pontic region, situated in the Lower Kuban basin. This study discusses the history of the vast chora of the Greek Gorhippia in the southeastern fringes of Sindica, focusing on findings from a Bosporan fort—the Raevskoye fortified settlement. We reconstruct the evolution of the anthropogenic landscape of the area over four centuries (Hellenistic and Early Roman period). The chronology is based on a collection of Bosporan coins from the fortified settlement. We analyze the factors due to which the habitation layers of the fortified settlement span a period from the Early Bronze Age to the High Middle Ages. We provide a new topography of the Early Iron Age aboriginal site, along with that of the fortified site existing during the three Bosporan stages. Special attention is paid to the fortification system, arranged in the Hellenistic period. Studies in recent decades have suggested that the fortifications were constructed according to the typical Bosporan technique of adobe-stone architecture. The fortified settlement evolved over a long period as an economic and political center of a large borderland zone between the Greek civilization and the archaic societies of the Caucasian piedmonta peculiar frontier of the classical era.