The potential for risky play and independent mobility to increase children’s physical activity, and enhance cognitive development and emotional wellbeing has been recognised for some time. The aim of this study was to describe the attitudes of New Zealand parents towards such risky play practices and independent mobility, the barriers preventing them from allowing their children to participate, and how often their children engaged in risky play activities. An online survey comprised mostly of validated scales and standardised questions was completed by a nationally representative sample of 2003 parents. We found that parents had neutral feelings about the risk of injury to their child through play, rather they were concerned about road safety and “stranger danger”. There was strong agreement that there are multiple benefits to be gained from exposure to risk and challenge, and that health and safety rules are too strict. However, 73% of respondents stated that their 5–12 year old child seldom or never engaged in four or more risky activities, and only 14.3% engaged in four or more often or always. While parents agree that their child is likely to benefit from risky play, they do not have the confidence to allow their children to engage in such activities. Future research should address barriers and fears when implementing strategies to facilitate risky play.