Local and regional governments in western European peripheral areas aim to spur leisure-led regional development. We explore planning for leisure by applying an evolutionary economic geography (EEG) approach from a complexity perspective. We identify conditions which enable and constrain leisure development and its effects on the region as a whole. This means combining the local level of individual adaptations with the institutional setting and with the regional scale. We examine the Dutch province of Fryslan and explore by means of case study analysis how current leisure development processes can be explained in a complex evolutionary manner. We explore economic novelty as a result of individual adaptations; how such adaptations through interactions create emerging spatial patterns; how these spatial patterns form self-organizing new types of order; and the way this process is dependent on previous paths whilst also creating new pathways. Our findings show that although development is dependent on individual adaptations often stemming from a few actors, for such adaptations to have an effect on the region requires a connectivity between actors and a sense of urgency amongst those actors. Using a complex EEG approach allows us to explain leisure-led regional development as the product of these conditions. This can help planners deal with the complexity and unpredictability of this process, focusing not on a desired end goal as such, but on creating the conditions in which a more autonomous development can take place.