The goal of the present study was to explore the social behaviours of inhibited children in familiar social contexts, including: (1) free play with peers at preschool and (2) social activities at home and in the community. The initial participants were N = 248 preschool children between the ages of 42 and 66 months. From this initial data, two smaller groups of inhibited (N = 12) and uninhibited comparison (N = 12) children were identified. These children were observed during free play at preschool and parents completed daily logs of children's social activities outside of school. Among the findings, inhibited children were observed to display more reticent (on looking, unoccupied) and anxious behaviours during free play preschool than uninhibited children. As well, inhibited children participated less in structured social activities outside school and were more likely to engage in dyadic play at home with a single friend as compared to their uninhibited counterparts.