In this research report, the authors explore an early childhood center as it transitions from a traditional playground to an outdoor classroom. Herein, the first phase of this qualitative research project is introduced and a central finding of adult perspectives is explored. The tension inherent in the various adult perspectives concerning the extent of structured lessons versus free play is exhibited. This finding has resonance within the larger literature concerning open ended and pedagogical play and further reveals the differing goals for children's outdoor experiences from teacher, administrator, and parent perspectives.