This multiple-case study describes the literacy events that occurred during play in three holistic preschool classrooms over a four-month period. The data includes field notes from observations and from discourse with participants, audiotape transcriptions, interviews, and writing samples. Analytic induction was used for the analysis. Within play, literacy was used as: a support for play themes, a frame for play themes, and as an extraneous aspect of play. Literacy events involved transactions with print, as well as social transactions. Social transactions within literacy events were analyzed for whether they involved: self-construction of meaning, joint construction of meaning, direct instruction, or challenge. The data show that in print-rich environments, where reading and writing materials are accessible, and where literacy is an expected way of life, teachers can meaningfully facilitate literacy development. The teachers capitalized on the many teachable moments that arose during play by carefully observing children and making relevant literacy-related contributions. The children explored and developed their own understandings about literacy, and at the same time, nurtured literacy development in their peers; literacy development was both personal and social. By themselves, and with support from peers and teachers, the children explored the functions and features of written language, they tested their hypotheses about written language, and they developed strategies used by successful readers and writers. Play was found to be a meaningful and effective medium for facilitating literacy development.