The purpose of this action research project was to determine the relationship between a three-year-old preschooler’s physical activity engagement and their ability to navigate risks and challenges in the natural playscape play area compared with the traditional playground. The decline of children’s physical activity over the past decade has influenced the research on the attributes of the outdoor space where children can become fully engaged as they navigate the risks and challenges encountered in their environment (Haga, 2021). A mixed-method study was used to determine significant differences in the children's physical activity engagement in a specific play area. Data was also collected on the preschoolers’ risky play experiences in each play space. Data analysis revealed a significant difference in physical activity engagement in sliding occurred on the traditional playground. Analysis of risky play engagement revealed significant differences in play with speed, play with impact, and disappearing play when comparing the two playground areas. The research findings from this study may prove beneficial for early childhood educators and managers to consider as they design outdoor play spaces for the students in their care. The outcomes may also provide information for educators and parents to consider as they facilitate outdoor play, actively participate with the children, and give preschoolers the training and scaffolding necessary to navigate risks and challenges during physical activity engagement. The conclusions provide evidence and information for early childhood stakeholders to consider as they determine solutions to reduce inactivity and obesity in young children.