This article discusses the role of play and imagination in three urban settings: an ELA classroom, a community organization grounded in civic participation, and a digital learning lab in a library setting. We draw on sociocultural theories of imagination to show that all of the affordances and constraints of the settings contribute to what could be imagined. All three settings were found to share the following overarching dimensions of engagement grounded in play and imagination: social actors have agency to act and transform signs and relationships as well as modify contexts in ways that change the problem space and their positions as meaning-makers; moreover, the emergence of unexpected meaning is developed in interactions of people, tools, and artifacts. The settings also point to differences in the nature of play and imagination related to other conditions of the setting. To determine these conditions, we developed an Activity System Observation Protocol that allowed us to analyze activity components such as objects, norms for action and interaction, tool use, distribution of labor, and the organization of community. We found that the object or purpose of each setting was integrally related to how play and imagination functioned in each.