This article offers interpretive perspectives on play as a cultural activity during middle childhood by contrasting two communities targeted for aid by external sport and play programs: a Chicago public housing community and a community of Angolan refugee camps. Ethnographic anecdotes, along with some survey results, demonstrate that aside from any organized programs, informal sport and play activities in each community were popular and culturally adaptive. In the Chicago community, where childhood was conceptualized as part of linear development toward adulthood, play was characterized by seriousness, competitiveness and individualism. In the Angolan community, where childhood was conceptualized as a discrete segment of the life course, play was characterized by an emphasis on inclusion and social roles. Contrasting observations from these two contexts serve to illustrate how sport and play can be a culturally valued part of childhood in distinctly local ways.