This chapter explores a visual reinterpretation that represents the complex physical environmental transformation of the Rocks in Sydney. As a famous historical site, the development of the Rocks is the result of the interactions of the social, economic and cultural changes in the past 100 years. It can be seen as the most representative example of urban-scape development of a historic city in Australia. Many previous studies of the Rocks mainly focused on heritage protection, historical events, the historical photography and documents collection. However the physical environment of the Rocks as a whole that witnesses the past changes has not been systematically studied. The general public cannot find the concise materials that can help them to understand the site. They are very critical to the current and future exercise of urban renewal projects of the site. The difficulty is how one can find an innovative way to effectively represent the research outcomes. This chapter highlights the visual reinterpretation as the key issue. Inspired by the art works of Escher, M.C. Escher has developed a special visual reinterpretation method in his graphic works. Based on a series of meaningful exercises, the chapter identifies the unique characteristics of the physical environment of the Rocks. Through revealing the layers of the Rocks, it classifies the main features of many restoration projects of the site into three essential categories. The developed visualization method provides an effective tool to deconstruct the multifaceted buildings forms, offering a new perspective to induct the general patterns of the complicated configurations and transformation of the urban historical site. The chapter’s outcome can be used as a valuable reference to direct future design intervention in an urban historical site.