The paper discusses some issues of automation of road network and structure of settlements representation on the multiscale maps. Using calculation of graphical load the critical scales for display levels of the road network are defined, line thickness is then modified, as well as a coherent geometric generalization of land use polygons is performed. Technique is formalized as a set of algorithms and implemented using Python programming language. Proposed methodology and software were tested using OpenStreetMap data. On the basis of analysis of the results strengths weaknesses of the approach are revealed as well as directions of its improvement.