This chapter discusses the significance of space and place in communication and expression and further explores how play can be used as a mode of critical inquiry. The first section demonstrates the potential of critical play using concepts from Walter Benjamin, Mary Flanagan, Ian Bogost, and Guy Debord as well as examples such as the film Do the Right Thing, the videogame Everything, and a designed-experience called Museum Hack. The second section uses this framework in an analysis of Disneyland, specifically exploring the ways in which the theme park both facilitates and inhibits visitors from playing in that place. The third section describes an activity called the Derivé in which participants design a place-based experience that is intended to help users discover new possibilities in familiar places. The activity encourages participants to understand place as a text that can be analyzed as well as a potential site for critical play.