Risky play provides various benefits to child growth and development. The culture of overprotection among Hong Kong parents have decreased young children's opportunities to engage in play that involves physically challenges. This study expanded our understanding of parents' views and behaviors on allowing their preschool children opportunities for risky play. Two hundred and three parents of children aged 2 to 8 years completed a questionnaire regarding their understanding and practices of risky play, and their attitudes toward risk-taking. Parents perceived risky play as more appropriate for boys at a younger age than for girls. Parents with higher education background were more likely to allow children to engage in risky play at a younger age. Moreover, a significant relationship was identified between parents' own attitudes towards risk-taking and the views on their child's age for involvement in risky play. Qualitative analysis further revealed that parents acknowledged the roles of risky play in enhancing physical development of children, and in having benefits for children's mental health. However, parents perceived risky play as something having possibility of leading to accidents. Implications on parent education relating to risk as an essential learning process on child development and as a way to build resilience are discussed.