In the province of Fryslân, like in many other rural or peripheral areas, leisure is seen as an important factor for regional development. However, planning for leisure development is a complex challenge, due to the fragmented nature of policies dealing with leisure and due to the location of many leisure activities on the fringes of urban and rural, and nature and agriculture. This paper uses a complex adaptive systems perspective to provide better insight in the dynamics of interaction between leisure and regional development. The paper is structured in four parts. The first part combines the literature on complexity and complex adaptive systems with evolutionary economic geography. The second part zooms in on processes of self-organization, co-evolution and emergence, as the focus of an evolutionary economic geography analysis. These processes are operationalized in the model presented in part three, which allows the description of a complex adaptive system at a specific moment in time in terms of robustness and dynamics, and unity and diversity. The fourth part argues for a qualitative historiographic methodology which reveals the way historical development shapes the complex adaptive system and changes its position in the model described in part three. This methodology is applied to the case of regional development through leisure in the Dutch province of Fryslân. The paper concludes that the integration of complex adaptive systems in evolutionary economic geography can lead to a better understanding of the interactions between leisure and other factors influencing regional development.