Located in the Putuo District of Shanghai, Caoyang New Village is an anomaly of sorts from the perspective of contemporary Chinese urban planning. With a history dating back to the early Mao era, the village has long been a symbol of socialist urban imagery that seems ahead of its time because in many ways it displays contemporary "new urbanism" elements. This paper discusses the origins and history of Caoyang Workers' Village, moving forward to its present conditions and recent role as an urban site for participatory planning. It also considers future redevelopment plans for Caoyang New Village, touching upon current conflict over the preservation of its cultural heritage and the need to address its housing issues. In analyzing the past and present of Caoyang New Village, questions of its future as a unique entity within modernity-seeking Shanghai arise.