This research was conducted with the aim of complementing the study of the topic of the history of civil engineering technology from the colonial period which explains thedevelopment of rail-based transportation networks, as well as the trial and error of new technology trials at that time. In this research, it is expected to obtain a basic and detailed explanation of the planning, location determination, and construction process. In addition, the research that took place on the Cirebon-Kroya railway line concentrated on the Notog-Kebasen segment reviewed the development of the railway network in Java which was closely related to the transportation revolution in the application of new technology in Java, including the construction system of tunnels, roads, and bridges (mentioned as wisdom buildings), located in the Notog-Kebasen area. The explanation in this research is presented in a chronological, systematic, and qualitative analysis, to examine the topic of the history of civil engineering technology in the construction of the railroad network, including the wisdom building. The construction of the Cirebon-Kroya railway refers to the law of December 31, 1912 Stbl. 32/(1913), in which the 75 km Cirebon-Margasari section was opened on July 1, 1916, the 51 km Kroya-Margasari section was opened on July 1, 1916, and the 32 km Patuguran-Margasari section was opened on January 1, 1907.