Making room for playful learning in school can be difficult. Formidable tensions exist between playful learning and the way pedagogy is currently structured in most schools. Educators often differ in how they value playful learning practices and their understandings of the nature of play. For, what is playful to one learner may not be experienced as playful by another. To those who view play as a central pathway for learning, resources such as time, space, and materials can seem in short supply. To those who see play as silly and off-task, encouraging playful learning can run counter to educational policies that emphasize efficient coverage of the curriculum. We believe that a pedagogy of play—a systematic approach to the practice of playful learning and teaching—is needed to bridge these tensions. Creating and operationalizing such a pedagogy requires a school culture where playfulness is celebrated, examined, made visible, and better understood as a powerful pathway of learning. Indeed, bringing play into a central role in a school entails creating a culture that values the core tenets of play: taking risks, making mistakes, exploring new ideas, and experiencing joy. The purpose of this paper is to share ideas that are emerging from a recent research initiative called a Pedagogy of Play that explores how playful learning can assume a central role in school.