Problems of research of the territorial development of the old-developed regions are due to the duration and extraordinary saturation of historical processes that flowed and continue in them. The study of changes in the territories of states and various entities is important not only for understanding the past: local and regional conflicts whose roots often go deep into centuries, remain for a long time and continue these days, territorial claims are relevant now. This is especially evident on the example of such regions of oldest development, as the Black Sea region. historic-cartographical studies, systematization of previously known and newly identified sources, the analysis of old geographical maps and plans allow us to form a holistic picture of the evolution of space, its territorial structure, as well as the functional role of one or another place in the past and present. In the article on the example of Bessarabia - the historic-geographical region of the north-Western Black Sea coast - the most important cartographic works presented, being key for certain stages of its historic-geographical evolution and development of cartography as a whole: the Antiquity and the Middle Ages (when the first geographical maps appeared), the 15^th - 18^th centuries (when the toponym under study was first applied into maps, and detailed topographic maps began to be created) and the 19^th - 20^th centuries (when political events again changed the semantics of the toponym Bessarabia). It is shown how geographical representations of the region transformed during different historical periods. The content of the toponym denoting region is considered, at different times related to different sections of the Black Sea coast and included various territories, as well as its use today as a political tool reflecting actual territorial claims.