The physical and social environment of children in cities is continuously changing. Knowledge about the positive effects of natural play experiences within the child's development is becoming widely known. Affordances of diverse landscape elements and especially loose parts for play in natural environments influence play activities. New concepts of natural playgrounds emerge and call for more research in this field. We conducted a comparative study on differently designed playgrounds (contemporary, naturally structured) in Bremen, Germany. The aim of the study was to further explore how diverse play environments afford different forms of play in kindergarten children aged between five and six years. Results show differences in number and duration of play episodes as well as in the occurrence of different categories of play. Existing observational instruments need improvement to adequately evaluate the impact of new playground concepts on early childhood activities.