This chapter explains when and why the Randstad’s contemporary spatial configuration developed. It traces the historical process of spatial transformation from the Middle Ages until the end of the twentieth century with the discernible trends being centre stage. The chapter describes spatial transformation in three consecutive governmental stages: the Middle Ages, the Early Modern age and the threshold to the Modern Era. As in many urban regions in Europe, the Randstad towns were a medieval creation. In the Randstad territory only Utrecht had evolved into a town in the very early Middle Ages. The Randstad configuration with four dominant towns – Amsterdam, Rotterdam, The Hague and Utrecht in this order – had become a fact. Medieval government contributed to the rise of this spatial configuration in several ways – and with various motives. In the hostile political environment of the late Middle Ages, local lords were forced into a continuous quest for ways to survive.