Approximately 36,000 Swedish children seek medical care annually because of injuries during school time. The purpose of this field study is to investigate risky outdoor play at the school yard and to describe teachers’ perceptions of risk and safety in relation to learning and development. The study includes observations of children (6–12 years old) during outdoor activities as part of the school’s activities and includes focus-group interviews with teachers and children. Children were seen climbing high in play facilities, speeding down slides, or competing with sticks in the woods. Different views of risk and safety among the participants influence outdoor play activities. Teachers’ knowledge of risk seems to be derived from common sense and personal experiences rather than from a professional perspective. A joint approach of educational and medicine disciplines is desirable when it comes to children’s health and development.