Outdoor play is considered an essential aspect of a 'proper childhood'. However, unsupervised outside play is declining, a decline attributed to parental anxieties about children's safety. However what drives these anxieties and how this impacts on contemporary outdoor play is less clear. Our paper seeks to explore this through an analysis of adult narratives generated through digital map-making and forum discussion about where they played as children and where they would allow a child to play unsupervised now. Our analysis explores the nature of these narratives and pivotal moments in which adults articulated the disconnect between their own recollections of idyllic spatial freedom and the spatial restrictions they place on contemporary children. This offers a rich understanding of how parents navigate conflicting cultural imperatives on risk-avoidance and children's rights to a 'good' childhood.