Children are born with an intrinsic drive and natural curiosity to explore the world around them. Just as young children are attracted to the natural world, they too are enticed by the physical challenges and risk-taking experiences that such environments provide. Based on research conducted at one of Canada’s first Forest Kindergartens and using Sandseter’s conceptualization of risk, this article aims to explore the safe risk-taking and risky play experiences of four children at a nature-based early years programme in rural Ontario. Not only does this research add to the growing body of empirical evidence surrounding risk and nature-based learning in the early years but also provides a unique Canadian perspective not often discussed in the literature. An incidental outcome of this work is exposing researchers and practitioners to the types of safe risk-taking and risky play experiences that may occur within an early years Canadian context.