Play is an inherently important early childhood construct. Play can support the effective development of relationships, cognitive skills, social competence and self-regulation of emotions and behaviours. Decisions about what types of play spaces children have access to are significant. Utilising naturalist observant techniques, event sampling and interviews, this case study focussed on the growing recognition of the unique properties of nature-play experiences in supporting young children’s well-being and development. The findings indicate that nature-based play is typified by interactions that are primarily unstructured, yet purposeful, rich in imaginative abstraction and symbolic interaction. Nature-play appears to facilitate positive social interactions and cognitive development by permitting differentiated spaces for a variety of focussed communications to transpire, thus facilitating well-being. Supporting previous research, the findings highlight the importance of pedagogues aligning their “nature dispositions” judiciously with that of the learning environment, as their beliefs, knowledge and interactive qualities directly influence children’s opportunities. This study recommends that early childhood education settings would benefit greatly from further, longitudinal research to explore and compare specific differences between children’s developmental growth in both natural outdoor and more formalised indoor environments, with a focus on overall well-being across all developmental domains.