The Leslie Street Spit is best known as an urban wilderness refuge but it has a fascinating, although obscure, social history. Archaeological methods are used here to uncover the material associations between the Leslie Street Spit and the City of Toronto. This approach reveals that the Spit reflects the past planning practice and creative destruction of the city. The Spit is found to contain artifacts of the past such as domestic items and rubble that resulted from slum clearing practices of the 1960s and development-driven planning practice of the 1980s. In its present state, the Leslie Street Spit acts as the romanticised ruins of the City of Toronto, composed of the material elements of the city that were discarded so that the new and “up-to-date” forms of architecture could take their place.