In today’s increasingly structured lifestyle, children’s play areas are greatly occupied with manufactured environments and predetermined games. On one hand, play is highly influential to human’s psychological development, however, many children are discouraged to play in natural outdoor environments, thus they are detaching from the nature. On the other hand, creativity is essential in many domains of today’s life, both in the individual level and societal level. Not only social environmental aspects influence creativity, but the physical environment plays a key role on human’s creative behaviours. This chapter aims to compare children’s creative play potentials and their engagement levels in two different outdoor play areas which are the natural environment and the built environment, to observe which one of these settings are more supportive to child’s creativity. In order to understand children’s creative behaviours, this chapter initially offers a critical review of various approaches to creativity, and underlines the most appropriate theory to be used as a scale for analysing children’s behaviours in the environment. Secondly, 15 nursery children are taken to two different outdoor settings for playing: 1- the woods, representing the natural play environment and 2- a traditional manufactured playground, representing the built play environment. Their levels of creativity are observed and analysed based on the chosen theory of creativity. The result of the critical study shows that Lubart’s theory of creativity according to his recent creativity test, Evaluation of Potential for Creativity (EPoC), gives the most inclusive explanation which covers a diverse range of aspects and can be used as a framework in order to analyse children’s creativity. The results obtained from the second part of the study show that the children were involved in higher levels of creativity and more engaged when they were in the natural environment compared to the built environment.