In the early 18th century, people saw childhood as a highly dangerous period to be hurried through – two-thirds of children died before they reached the age of five. Towards the end of the 18th century, child mortality rates fell dramatically and suddenly childhood became associated with freedom, creativity, emotion, and malleability. People began to think differently about play and children's capacities. Today's children spend much less time playing outdoors than their counterparts did 50 years ago. Outdoor play in the community is in decline and, at the same time, mental health issues are rising rapidly. This chapter presents observations of outdoor play at settings in Scotland, Thailand, Wales, France, England, and the Netherlands.