This paper deals with the analysis of the themes and codes characterizing the graphic/textual description of the cities and their fortifications, as well as narrated in The Hundred Town of Italy, the illustrated monthly supplement of the “Il Secolo” (Le Cento Città d’Italia, supplemento mensile illustrato del Secolo). Published in Milan by Sonzogno, between 1887 and 1902, the 192 four sides supplements still provide a vivid descriptive picture of the nation, at the turn of the nineteenth and twentieth century. Despite the poor quality of most of the illustrations in these sheets, they have acquired, over time, an appreciable documentary value. Therefore, a critical reading is capable of giving a new knowledge about the systems of fortifications in Italy. The performed analysis of places and cities is characterized by a descriptive storytelling of the fortifications, highlighting the specificity of communication and perception. What emerges is a strong landscaping connotation given to the city-fortification system in a socio-political reality, during a historical phase of transformation. The survey highlights how this architectural heritage can still be valuable cultural element, not only for the territory