Freeways that once tore through the urban fabric are now reaching the end of their lifespan and raising the question as to whether it is time to rebuild or remove them. The Interstate system has revolutionized transportation, connecting cities nationwide, but at the same time has slashed through existing neighborhoods. The very land from which hundreds of Fox Point residents were evicted for the construction of Interstate 195 through Providence, Rhode Island, now lies barren as a result of the interstate’s realignment. The surplus land, rezoned as the East Side Overlay District (ESOD), connects the Providence River and Narragansett Bay waterfronts. The ESOD is awaiting request for proposals (RFP), presenting an opportunity to redefine sustainable community development for Fox Point’s waterfront. The latest research on sustainable development employs culture as a direction for environmental, economic and social vitality. This project utilizes the historic urban landscape approach as a framework for providing knowledge and planning tools, for a more informed decision making process. In response, a proposal for redevelopment merges cultural development with visitor interaction in a reactivated waterfront. The post-freeway city has an opportunity to rebuild sustainable communities through cultural infrastructure.