A risk-averse philosophy and practice towards children playing and learning in natural surroundings predominates many parts of the educational world. In schooling, the concepts of risk and risk management have created the false impression that there's something inherently dangerous about learning in natural surroundings. The purpose of the current study is to examine parental attitudes that involve encouraging their children, ranging from preschool to Grade 8, to experience natural surroundings. A case study approach involving in-depth interviews, using semi-structured questions, with twelve Canadian parents was utilised. A constant comparative analysis identified three broad themes: (1) parents expressed a risk-tolerant approach to children playing and learning outdoors; (2) parental views on the benefits of outdoor playful learning; and (3) parental confidence in allowing children to play and learn in the outdoors. In the discussion section, it is then argued that rather than allowing the concept of risk management to misleadingly dominate this learning environment, this phenomena should be reconceptualised as 'nurturing embodied experience'.