The urban landscape of center city Philadelphia can best be described as a series of concrete thoroughfares –pathways to other places. Vast spans of impermeable surface intended for pedestrian walkways and social hubs are vacant, under appreciated, and wasted. This thesis aims to address these problems by synthesizing research gained from a review of literature and human centered design methods conducted in the field such as interviews and observations. Using play as a design strategy we discovered new ways to generate user feedback, make site observations, catalog data, and strengthen a sense of community, even if temporarily. We believe that with a little creativity and motivation, people can revitalize their space. Play is sparks innovation, improves social interactions, is fun and free! By using acts of play can we stimulate urban environments and improve peoples experiences in a city? We were about to find out.