Background: Research into digital practices and cultures repeatedly calls attention to the complexity of communication spaces and meaning-making practices. With the blurring of boundaries between online and offline, these entangled practices involve the interweaving of human, material, semiotic, and discursive practices. Purpose: This introductory article builds on theoretical work by Huizinga (1950/2014) and Appadurai (2001) and presents the concept of playscapes to help situate the overall collection of articles in this special issue, Virtual Convergence: Synergies in Virtual Worlds and Videogames Research. Research Design: This analytic essay examines virtual worlds and videogames and offers the concept of playscapes to expand the discourse about space and finitudes of practice. Conclusions: Playscapes extend current conversations about learning, transmedia, and play ecologies because playscapes can support the discussion of entangled meaning making across space and time, all the while acknowledging the situated nature of the activity.