Trains with different numbers of cars running in the open air were simulated using the delayed detached-eddy simulation (DDES). The numbers of cars included in the simulation are 3, 4, 5 and 8. The aim of this study was to investigate how train length influences the boundary layer, the wake flow, the surface pressure, the aerodynamic drag and the friction drag. To certify the accuracy of the mesh and methods, the drag coefficients from numerical simulation of trains with 3 cars were compared with those from the wind tunnel test, and agreement was obtained. The results show that the boundary layer is thicker and the wake vortices are less symmetric as the train length increases. As a result, train length greatly affects pressure. The upper surface pressure of the tail car reduced by 2.9%, the side surface pressure of the tail car reduced by 8.3% and the underneath surface pressure of the tail car reduced by 19.7% in trains that included 3 cars to those including 8 cars. In addition, train length also has a significant effect on the friction drag coefficient and the drag coefficient. The friction drag coefficient of each car in a configuration decreases along the length of the train. In a comparison between trains consisting of 3 cars to those consisting of 8 cars, the friction drag coefficient of the tail car reduced by 8.6% and the drag coefficient of the tail car reduced by 3.7%.