Article is devoted to historical geography of the Kargopolsky district of the middle of the XVI first quarter of the XVII centuries the Kargopolsky district was created in the basin of the river of Onega, stretched from the South - from the Lake Lacha for the North to coast of Onega Bay of the White Sea. In the West the district bordered on Zaonezhsky country churchyards; in the east - with the Dwin district; in the southeast - with the Vazhsky district; in the northeast - with the Dwin district; in the south - from Charondskaya okrugy and the Belozersky district. The historical geography studies areas in their historical development: as geographical conditions are connected with processes of colonization of lands; the reasons influencing development of the territory during various periods of history that allows to predict further development of the region in the economic and historical and cultural relation. Relevance of research is defined by it. Scientific novelty locates that the actual material is systematized and to be introduced into scientific circulation the new data from written sources connected with historical geography of the Kargopolsky district. In the Russian historiography the territory, borders, internal structure and a control system of the district were defined, settling and economic development of separate areas of Poonezhya was investigated. There were not up to the end studied questions connected with definition of internal borders, features of economic development of certain territories of the district and development of settlements, localization of means of communication and their roles in colonization of lands. As a result of the conducted research the new facts and assumptions were elicited. And a volostok allowed to establish to geography of volosts the area of the most intensive and possibly early development, so-called «the Onega massif». Connection of «the Onega massif» with the ways passing through it water snaking trail is shown, their value in settling of the district thereby is emphasized. To the middle of the XVI century in the Kargopolsky district, generally around Kargopol the network of roads is already formed. In northern part of the district overland ways still a long time were called as snaking trail. The probable border (boundary) between half of the Kargopolsky district was defined: Turchasovskoy and Kargopolskoy. An attempt of reconstruction of history of development of the Kargopolsky district during the Novgorod period is made: boyarshchina - possession of peasants-svoyezemtsev; names of settlements the village or seltso - the former administrative centers or possessory settlements; localization of the Novgorod Pogost at a threshold contacts Berichevsky thresholds in the lower reach of Onega and the volost the Ordomsky country churchyard in the Turchasovsky camp.