This small scale research project examines opportunities for creative thinking and imagination through den making in a rural private day nursery with its own woodland area on the borders of England and Wales in the UK. The research is underpinned by sociocultural theory and is an ethnographic study of non-participant observations of children aged between three and four years old and early years practitioners involved in supporting their play. The focus is on children’s creative play in peer social groups and examines the way in which children explore their environment and utilise their play space and resources to sustain imagination and creativity. The research considers how the environment and den-making context provides opportunities for possibility thinking [Craft, A. (2001). “Little c creativity.” In A. Craft, B. Jeffrey, & M. Liebling (Eds.), “Creativity in education” (pp. 45-61). London: Continuum], where children are encouraged to explore “what if?” questions. The research explores the way in which an outdoor environment can support flexible opportunities and resources where children are able to engage in imaginative and creative play, develop their communication skills and build relationships with other children and adults. The research considers children’s fascination with the story “bears in the wood” and how early years practitioners facilitated their creative thinking and imagination.