In our rapidly changing contemporary society, it has become apparent that children spend significantly less time playing outdoors than their parents did. Therefore, considerable attention must be paid by professionals to engage this challenge, especially within early educational contexts. The goal of this study was to first explore the continual drive of play in educational growth and, second, the ways in which children play outdoors at school, in order to reap the developmental benefits of outdoor play in a supportive context, where such fundamental activity is not only allowed, but also supported. The results of this study reinforce existing research in this area, highlighting the findings of children’s physical play behaviour and its frequency, also in connection with the use of tools and toys; further findings highlight teacher’s attitudes and suggest several options for early childhood professionals to foster children’s enjoyment of outdoor play. Finally, the study results have implications for future opportunities in the planning of active spontaneous-play.