Increasingly concerns are expressed about the formalisation of early childhood education and the loss of opportunities for children's play in a range of European and European heritage countries. This paper takes up this challenge by discussing, from a cultural-historical perspective, the relations between play and learning in pre-school settings. A theoretical discussion of practices and affordances of a Conceptual Playworld, grounded in a cultural historical conception of play, is presented. New concepts are needed for understanding the relations between play and learning in pre-school settings, where the focus has traditionally been on play as the leading activity. Theorised are four key characteristics that emerge from the practice of a Conceptual Playworld illustrated through a practice example of Charlotte's Web. In this context, it is argued that imagination in play is foundational for imagination in conceptual learning, and therefore play-based programs make a key contribution to the development and learning of the young child.