This study looks at the influence of outdoor time on preschool aged children’s physical, social and emotional development. The researchers’ aim was to examine preschoolers’ physical, social and emotional development in the setting of their interactions with various environmental affordances and their peers over a one year period. The children’s activities were observed in two natural outdoor environments: a creek next to the preschool and a trail along the river in a nearby national park. The study assessed sustained and complex interactions in the children’s immediate environment, over time, and included a number of developmental outcomes. Results showed confidence of children in this study increased with accrued experience and shifted from focus on their own abilities to a greater awareness of others and increasing social collaboration. The findings also illuminate the importance of varied and challenging environmental affordances for children’s free play and movement. This research suggests that early childhood educators should be encouraged to provide a diverse range of outdoor environments for children’s play, with shifting degrees of risk, to increase children’s developmental opportunities not only in the physical domain but also in a social context supporting resilience and emotional wellbeing.