This three-article dissertation explores the nuances of play within adventure playgrounds, guided by two pivotal questions: how does play manifest in settings with user-negotiated boundaries, and how do the creators of these playgrounds perceive play? Utilizing a mixed-methods approach across three articles, this study explores the interaction between the physical and conceptual boundaries of play spaces, the perceptions of playworkers, and the play behaviors and experiences of the generations of players. The research methodology combines sociolinguistic analysis, participatory observation, multimodal making, and interviews. The first article examines the linguistic landscape of adventure playgrounds to understand how language influences the play environment. The second investigates the players’ perspectives on play within these unique settings. The third article focuses on playworkers, analyzing their perceptions and practices in facilitating play. Findings reveal a complex ecosystem where space, perception, and play are intricately linked, highlighting the role of user and creator in shaping the boundaries and possibilities of play.