The article describes the experience of the topographical mapping of railways in Russia and the USSR. The development of railways representation on topographic maps is traced in the tables of conventional symbols for the period from 1853 to 1983. The study covers the analysis of the map symbols of metric scales (1:25 000, 1:50 000, 1:100 000) and non-metric scales (1:42 000, 1:84 000, 1:126 000). Classification criteria for railways on topographic maps are covered. It is established that this classification gives an indication of the traffic capacity of the railway infrastructure and is based on the features that are essential for the characteristics of the landscape. The retrospective analysis was carried out based on the following classification grounds: rail gauge; number of tracks; kind of traction; route availability. In addition, the development of the symbols of operation points and halt platforms is considered. The study was carried out taking into account the features of the development of the railway network of Russia and the USSR. It is revealed that the development of the system of symbols went on the way of changing the number of classification criteria, and also quantitative and qualitative indicators within the classes. It is obvious that the design of the conventional symbols is «catching up» with the development of railway infrastructure. As a result of the development of conventional symbols of railways the complexity of their execution was reduced. That is often interfered with the clarity and the logic of construction. The main proposals for the improvement of conventional symbols are formulated. It is concluded that it is necessary to revise and supply the outdated tables of conventional symbols for reaching the complete and visual representation of railways, taking into account the use of geoinformation mapping methods.