This article presents a proposal for using digital cartography applied to the comparative analysis of a series of 13 historical maps of São Paulo city. The analysis sought to establish links between the rail transport infrastructure and the process of structuring the city of São Paulo between 1870 and 1930. Therefore, we produced thematic maps from a selection of historical maps of the city and the following were identified: urban sprawl, existing neighborhoods, planned housing developments, paths design, railways and streetcars. It proved to be a practical way for digital cartography to be supported by Geographic Information Systems made more agile for handling, visualization and overlapping information in different historical maps, facilitating the comparative analysis process of the structuring role of paths and trails in the formation of the urban area, the work hypothesis verified at the end of the article.