Semarang City is a fascinating city to be studied historically through various aspects, including transportation problems. This paper tries to examine the condition of the transportation network in Semarang at least in the first 30 years of the 20th century. The main problem in this paper is how the condition of the transportation network in Semarang and its impact on Semarang people in the early 20th century. So far, the concern about historical studies in Semarang regarding transportation has always been regarding the railway network centered in this city. However, the railway network is only connecting Semarang with other areas in Central Java and beyond. What about the transportation conditions in the city of Semarang itself?. Of course, the train is not the primary mode if we talk about transportation mode inside the city. In the land transportation network in the big cities in the Dutch East Indies at the end of the 19th century, the mode of transportation using animal power played a huge role. However, changes began to occur when modern transportation modes, such as bicycles, motorbikes, cars, and trams, entered the Dutch East Indies, including Semarang City, at the beginning of the 20th century. The significant impact that occurs is that this mode of transportation provides a new network pattern in transportation, especially the land transportation network in Semarang. This study uses the historical method, which consists of four stages: heuristics, source criticism, interpretation, and historiography. The results of this study indicate that there are complex dynamics in the development of land transportation in Semarang, besides that technology plays an essential role in this development.