Risk-taking during the toddler years is crucial for the development of autonomy, initiative, and independence. However, the current culture in the U.S. seeks to minimize the risks young children are exposed to. This small-scale, mixed methods study examined parental attitudes towards toddler risk-taking and children's behavior during nature play. Each child in a young toddler classroom at a northern New England childcare program (n = 9) was observed for 90 minutes and their parents (n = 17) surveyed. Results show a wide range of risk-taking profiles for children in the same classroom. Parents were more concerned about children's play at heights and least concerned about rough and tumble play, the most and least frequent activities children engaged in. Parents who rated outdoor play scenarios as more risky tended to have children who exhibited more risk-aversion. Suggestions for working with parents to understand the benefits of risk-taking in outdoor play are discussed.