Playing outdoors is an essential component of childhood yet that play is often bound by adult perceptions of safety, risk, and children’s capabilities. Research reflects the positive value that playing freely outdoors has in terms of children’s overall development. However, literature also highlights the impact of a societal focus on safety, which can limit young people’s access to the outdoors and the types of play that they seem to enjoy. The tension that can exist between pedagogical practices and trusting children to be safe plays out within the structure and format of this paper as the motifs of bounding and resistance that can exist in both research and play are unearthed. Drawing on autoethnographic and narrative approaches I explore, share, and reflect upon outdoor play experiences from my own childhood as a means to gain a deeper understanding of how children were and are positioned in society and communities.