This chapter analyses port competition from a hinterland perspective. It focuses on a set of countries of Central Europe for which there is not a clear geographical advantage of one port over another. Such contestable hinterlands seem particularly relevant for an appreciation of factors that can tip the balance in favor of certain port alternatives, minimizing the statistical noise induced by distance effects. With the expansion of the European Union towards the East and the subsequent development of East-West transport links, such as the Rhein-Main-Danube canal, increased competition between ports can be expected. This paper tests this idea for different industries, by using a spatial interaction model on data on container shipments to the United States. Sailing frequency is used as a measure of port attractiveness and truck drive time as geographical separation. We also identify preferential ties between source countries and ports and barrier effects in the organization of hinterlands. Against expectations, the results highlight the path dependence in the North-South organization of hinterlands, with a persistent split between Switzerland, mostly oriented towards Rotterdam and Antwerp, and the other countries of Central Europe, historically tied to German ports, while Mediterranean ports are largely disregarded.