For urban transportation planners these are challenging times. Mounting practical concerns are mirrored by more fundamental critiques. The latter comes together in the observation that conventional approaches do not adequately account for the irreducible uncertainty of future developments. The author’s central aim is to explore whether and how an evolutionary approach can help overcome this limit. Two core hypotheses are formulated. The first is that the urban transportation system behaves in an evolutionary fashion. The second hypothesis is that, because of this, urban transportation planning needs to focus on enhancing the resilience and adaptability of the system. Changes in transport and land-use development patterns and policies, and in the broader context of the postwar period in the Amsterdam region, are analysed in order to illustrate the two core hypotheses. More general implications are also drawn.