The article provides a comprehensive historic-geographical, toponymic and architectural analysis of a unique monument of medieval religious and defensive architecture - the Church of the Assumption of the Virgin in Vasilkov on the Dniester and its surroundings, located on the modern state border of Moldavia with the Ukraine, and in the Middle Ages it served as the border point of the principality of Moldavia with the Grand Duchy of Lithuania and the eastern outpost of the capital of the tsinut (county) of Soroky and its main fortification - the Soroka castle. The architecture of the rural temple with a bell tower, erected on the elevated cape with steep slopes, is a rare example of a preserved structure that combines the traditions of wooden architecture based on the proportions used in antiquity for the construction of stone churches. The medieval fortified point with a unique monument of the cult-defensive architecture together with a courtyard, a trading square, as well as an ancient trade road and a river crossing represent a united natural and historic-cultural complex. The solution of historic-geographical puzzles enveloping the monument of heritage is based on a comprehensive multiscale historic-cartographical analysis and the use of modern geographic information methods, including comparison of topographic maps with aerial and satellite images of the terrain, as well as high-precision digital elevation models, hydrography and other cartographic products. A method of comparing cartographic images of an area in chronological slices (in different historical periods) is supposed to be highly effective. It allows you to observe the historic-geographical evolution of the area. A research of the complex of toponymic problems associated with the territory under study reveals the processes of massive transfer of geographical names in antiquity, covering not only the north-Western Black Sea region and adjacent territories, but also much wider spaces of the east european plain, where modern toponymic landscapes were formed.