Play is an essential part of childhood. It is through play that children explore, experience, learn, and develop. An important element of play is unpredictability. Much of children’s play is about crossing boundaries, stretching limits, trying new things, and putting themselves to the test, Children seek risk experiences and thrills through play. This chapter focuses on what risky play is and how children engage with and handle risks. It also discusses how children’s opportunities to engage in risky play have changed during recent decades, where adults are increasingly restricting children’s freedom to explore. Concerns for safety have become more dominant than the willingness to protect children’s right to play.