All people influence, and are influenced by, the contexts they inhabit. Leisure contexts are no exception. The current research comprised three studies investigating the links between one leisure context, skate parks, and adolescent development. Using interview, observation, and questionnaire methods, the research shed light on several of the demographic, psychosocial, and subcultural correlates of skate park use. Despite polarized attitudes to skate parks, parks users reported levels of personal adjustment and social integration similar to those of other adolescents. The research illustrates the need to distinguish between different types of unstructured youth leisure activities, with those activities that occur within the unstructured context of a skate park shown to offer considerable potential for positive youth development. (Contains 5 tables, 1 figure and 2 notes.)