Skywalks are a unique typology of second-level pedestrian networks that link parking and downtown destinations. They were implemented throughout North American cities to attract pedestrians and sustain retail in central business districts. The rarity of skywalk systems, their relevance to the particularities of American urban design and their position at the intersection of major concerns of the American city: traffic, downtown revitalization, and identity (Fruin 1971; Robertson 1994; McMorough 2001) provided the departure point for examining skywalks as heritage. As the viability of skywalks is questioned, this study employs a toolkit based on the theory and values of heritage preservation to evaluate skywalks as built heritage. The results are used to recommend scenarios that utilize the significance of skywalks to take them into a new cycle of sustainability through re-use and preservation. These findings are meant to offer urban planning professionals, local government decision makers, real estate developers and grassroots organizations a new perspective and a new resource to aid in the continuous challenge of dealing with the contested heritage of skywalk systems.