Childhood is a time of vulnerability, unknowns, and vast potential. Children’s environments should be sensitive to these qualities. This thesis is an investigation of outdoor play environments for children. Its focus is the design of environments that encourage playful attitudes that enrich the process of children’s development. In the past, children played freely outdoors and explored natural environments. With the growth of urban living, playgrounds emerged in cities as places for children to play. Today’s conventional playgrounds are not responsive to the child’s needs to experience the unknown, imagination, and creativity. In these playgrounds, use is predetermined, and activities are imposed, hence they do not enhance children’s rich sense of curiosity and playfulness. Friedrich Froebel argued that play is the highest stage of the child’s development. This thesis studies play and its role in the child’s healthy development by exploring the characteristics of natural and built environments for play. The design of an outdoor play area is intended for children aged two-and-a-half to six years old, when play has a crucial role in physical, cognitive, social and emotional development. The thesis is sited in suburban Toronto, adjacent to a preschool childcare facility. It uses topography and natural elements, and investigates strategies to integrate them with built elements. It also investigates the values of free roaming versus safety in the early childhood experience. The goal of this thesis is the design of an outdoor play environment that will enable children to regain their sense of freedom of movement and exploration through play.