The authors studied sex-typing in the kinds (e.g., sports, handicrafts) and social contexts (same- vs. other-sex companions) of children's free time activities, and the links between sex-typed activities and gender development over 2 years. Participants were 200 White, working- and middle-class children (103 girls, 97 boys; mean age = 10.86 years). In annual home interviews, children rated their self-esteem, gender role attitudes and sex-typed personality qualities, academic interests, and school grades. During 7 nightly phone interviews each year, children reported on their activities. Boys were more sex-typed than girls in their peer activities, and children were least sex-typed in their activities with siblings. Sex-typed activities in middle childhood predicted individual differences in gender development in early adolescence.