The authors discuss and analyse the complex interplay between rail transport and urban development around railway stations in the Netherlands. Although this interrelationship, known as transit-oriented development (TOD), has been theorised and studied in the academic literature, the complex and dynamic underlying mechanisms and the appropriate planning and management responses have yet to be understood sufficiently. This is particularly relevant for local, regional, and national policy makers in the various planning subsystems. In order to improve the understanding and management of the dynamic relationship between rail transport and urban development, a conceptual model of TOD was developed. Actors validate and learn from this model in the serious game SPRINTCITY, in which a rail corridor is developed over a period of twenty years. It is hypothesised that playing SPRINTCITY helps actors to understand factors, other actors, and potential barriers related to TOD. Research data were collected through debriefings, questionnaires, and model output from more than thirty sessions conducted between 2010 and 2012. The authors conclude that the combined and iterative use of modelling and gaming was effective from the perspectives of design (development of the TOD model), research (insight acquired on TOD), and policy (policy-oriented learning and analysis).