Greater Sydney Parklands (GSP) delivers nature education holiday programs to primary-school-aged children. The Bushrangers holiday programs are based on the premise of educator-guided, child-led nature play and are developed with a grounding in nature pedagogy. Centennial Park is one of the urban park sites that offers these programs across the GSP estate. The outdoor classroom space where this occurs is a casuarina forest with tree stumps, roots, natural foliage, and a climbing tree. Risk-taking, including physical risk-taking, is promoted throughout the Bushrangers activities, materials selection, and play provocations. In a recent school holiday period, GSP educators conducted structured observations using Sandseter’s (European Early Childhood Education Research Journal, 15, 237–252, 2007) risky play categories to further develop their understanding of how physical risk-taking was occurring in the programs, and how it could be improved and promoted. Children in the programs were observed jumping off fallen logs, climbing a tree, running over uneven ground, and exploring the boundaries of the outdoor classroom. After analysing the observation data, the three main areas that were found to enable risky play to flourish were (a) educator-guided, child-led play; (b) play affordances; and (c) connection to place, self, and others. To ensure the continued focus on physical risk-taking in programs, educators conducting future Bushrangers programs will offer children deeper support and an opportunity to discuss risk-taking in end-of-session reflections. Educators will repeat these risky play observations in 12 months to ensure a consistent approach to pedagogical practice, and continued focus on physical risk taking within programs.