This article addresses the complexity of children's risk landscapes through an ethnography of 10- to 12-year-old Danish children. The data revealed how children individually and collectively engaged with risk in their everyday activities. The children assessed risks in relation to their perceptions of their health as strength and control, negotiated the conditions of playing, and attuned their responses to situations of potential social and physical conflict. In the paper this risk engagement is illustrated in a variety of contexts: children's decisions to wear or not to wear a bicycle helmet; playing and games and routine pushing and shoving at school. In looking after themselves, children negotiate rules of participation and they safeguard personal and collective interests. Gender differences in these processes are addressed and discussed. The article argues that risk engagement is an important resource through which children also learn from their own mistakes. This is a necessary learning process when children engage with their personal health and safety. The article critically discusses different sociological frameworks and shows the significance of the study for the growing literature on understanding the meaning of risk in childhood.