Forest schools are becoming popular outlets for families and teachers seeking a way to connect children with free play experiences. The author questioned how much she could step back and allow children to plan activities and make decisions, including those that carry an element of risk. Could everyone experience a sense of freedom? The subjects of this study are two groups of children in summer camp. A variety of techniques were used to define boundaries and establish relationships and trust. Practical considerations included physical and emotional health and safety, and public and family perceptions. Tools of inquiry included asking questions of the students, taking daily notes, and making weekly reflections. Photography, videography, written notes, and emails were sources of documentation. Children in this study were able to express their own interests and act upon their goals. There are further implications for forest schools and traditional programs in that it shows that feelings of fear are something that one can identify, work through, and overcome.