The article discusses the results of the application of geoinformation technologies in the study of the historical geography of the Upper Volga and Upper Podvinya of the late XV – first half of the XVII century. The study included the development of historical GIS of Tver, Toropetsky, Rzhevsky, Novotorzhsky, Belsky counties and the Tver half of Bezhetskaya Pyatina. The main sources are scribal descriptions of the end of the XV - the first half of the XVII century, the assembly material is involved. Localization of toponymy of the XV-XVII centuries was made using sources of the XVIII-XIX centuries. The objectives of the study included the characteristics of the territorial organization of the studied territory of the Late Middle Ages and early Modern times, including the localization of territorial administrative units, borders, roads; characteristics of rural settlement, territorial organization of the peasantry in historical dynamics; identification of the features of the historical geography of land ownership in the region. The result of the use of GIS technologies in historical and geographical research, in addition to web GIS of applied importance, is the characteristic of the territorial-administrative and settlement structure of the region, which has both all-Russian and local features. Among the local features are specific types of territorial organization inherited from the pre–Moscow period - digests and dozens that persisted in the XVI-XVII centuries. in the Upper Podvinye and on the southeastern periphery of the Novgorod land. A dispersed settlement system was characteristic of the Upper Volga region, while a "nest" settlement system was identified in the Podvine region. The different nature of the entry into the Russian state determined the peculiarities of the formation of local land ownership in the studied areas. Archaic features are also evident here (in the preservation of official land ownership in the Mikulinsky camp-county).