Cultural events, and in particular mega events, have long been an integral part of urban agendas as tools to foster economic development and urban regeneration in the context of inter-urban competition within capitalist economies. Policy makers in European coastal or port cities of any scale appear to be particularly keen on bidding for City/Capital of Culture titles. City/Capital of Culture events, as well as other hallmark events, should be understood longitudinally within cities’ experiences of culture and regeneration. In European medium-sized coastal cities, such events may be remarkable pivotal moments and may contribute to triggering long-term physical, socio-economic, and symbolic transformations. Despite the fact that cultural events and mega events alone are by no means sufficient to tackle structural challenges in European medium-sized coastal cities, it appears possible to argue that certain large-scale events can help local policy makers cope with issues of external perceptions and geographical and symbolic isolation.