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In the paper considered gravestones with epitaphs of the end of the 15 th—16th century from Kashin (modern Tver region), which are an important source of medieval Kashin’s topography. In this regard the paper looks into the question Kashin city structure history and the directions of its development in the 15th — the end of the 16th century. On the basis of the sources along with epigraphical monuments are put in the sources published so far and among them — annales, lives of sacred from Kashin, acts from monastic archives, Census book of church lands of Kashin of 1621, and also the results of archaeological researches which report about the earliest elements of Kashin’s city building of — ostrog, churches and monasteries which existed in the last third of 14th — the beginning of the 17th century. From them the most ancient are city ostrog (built anew in 1392/93) and the Uspensky monastery (the first mention — 1368). The subscriptions gravestones connected with ancient necropolises, add to the list the first mentions of the Dimitrovsky monastery (1491), list churches st. Forty martyrs of Sevasty (1537), st. Ioakim and Anna (1594) and the Signs of the Mother of God (1594). Data of sources shows that in the last third of 14th — the end of the 16th century Kashin’s territory developed from the downtown in four directions. The northern, the east and the southern directions are obviously synchronous to each other. The southwest direction which, probably, developed less intensively is less documented by sources. The remained sources show an asynchronical emergence of separate sites of the city building and disprove the idea spread in local history literature, of the existance of Kashin “sacral plan“, which is allegedly was prêt as a platform for the building planning of the city. In the paper periods of active city planning connected with the activity of Princes of Kaschin Vasily Mikhaylovich (1319-1349/50) and Yury Ivanovich (1504-1533), and also the Prince of Tver Boris Aleksandrovich (after 1398-1461) are allocated.