This study contributes to the understanding of early childhood educators’ and parents’ attitudes and practices in relation to outdoor risky play for children. This study included 26 early childhood educators and 112 parents in rural and metropolitan areas of Australia and the United States. Participants completed an online survey about their perspectives and practices related to the provision of opportunities for children to engage in outdoor risky play. Questions also investigated reasons that prevented participants from providing such opportunities for children. Findings indicated that most educators thought it was important for children to be provided opportunities for outdoor risky play and did provide appropriate activities. Types of outdoor risky play opportunities fell into the categories of supporting large motor skills, supporting free exploration of the environment, and supporting assessment of risk. However, educators located in Australia rated outdoor risky play opportunities as significantly more important compared to educators in the US. Many parents also felt outdoor risky play was important and provided appropriate activities. Opportunities provided by parents fell into the same categories as educators, with additional features of nervousness and a desire to avoid hovering. Many parents identified the young age of the child and safety concerns as barriers. Implications for research and practice are discussed.