Importance. Based on the analysis of written and graphic materials of the Russian State Archive of Ancient Acts, it is proposed to consider the circumstances that influenced the drawing up of drawings in the key section of the Belgorod line – the territory of the Field in the Dnieper-Don interfluve.Research Methods. The methodological basis of the research is based on the desire to comply with the principle of consistency (involving a comprehensive consideration of facts, taking into account their development, relying on the structural and functional features of the subject), the principle of historicism (which is based on the study of historical phenomena, events and processes in accordance with their chronology and interrelation), the principle of objectivity (based on the fact that the sources and facts have objective content that allows us to reconstruct the historical past). The research is based on such general scientific methods as analysis, synthesis, generalization, and systematization.Results and Discussion. The totality of available information about drawings allows you to divide graphic materials into drawings of one city, a group of cities and individual localities. At the same time, the information content of graphic materials is directly related to the purposes of their compilation. If it is necessary to reflect the fortifications in the county, then only they are shown, although they are surrounded by arable land and the lands of serving people. This is a direct consequence of the fact that the fortresses and fortifications are under the jurisdiction of the Discharge Order. Arable land, hay mowing and other lands that are in use by serving people were taken into account in the Local Order. Such circumstances can be called the main factors influencing the information component of the drawings. The economic development of the territory went on in parallel with military defensive measures, despite the danger, the population sowed and harvested bread, moved around the territory for their needs, including beyond the line. The preparation of drawings in the 16th–17th centuries is an integral part of urban planning activities, sources allow us to identify two blocks of circumstances under which cartographic material is compiled: 1) upon inspection of large territories by special expeditions from Moscow and making copies according to available paintings and drawings covering large areas of copies of individual localities; 2) drawing up drawings during revision inspections of existing fortress cities and structures on their borders.Conclusion. Two types sources consideration through the structuring of materials according to the chronology and informativeness of a particular region made it possible to identify a number of drawings with the circumstances of their compilation and events occurring during this period in a particular territory. The considered examples, the proposed conclusions and conclusions make it possible to significantly expand the knowledge and importance of cartographic materials in the general system of state construction of fortress cities. At the same time, significant material has been identified that allows in the future to expand the designated topic, show the history and fate of drawings for a number of cities of the Belgorod region.