This study discusses the behavior of railway users who commute to work or school as they choose a station on the way home for eating or shopping. A quantitative grasp of the tendencies in this selection based on personal attributes and time points was obtained by creating models that accounted for the geographical relationships between individuals’ residences and their workplaces or schools, and for the environments surrounding stopover stations. It was found that the increased time required for a stopover, or the number of transfers between trains were points of resistance and that the fact that a station on the route home was a transfer station, and the extent of commercial space near that station, affected the attractiveness of that station. The results of a simulation applying the stopover station selection model, indicated that an increase in the commercial establishments near a station and the availability of interconnected railway companies affected the attractiveness of a stopover station.