Australia is a settler society where the rural-urban fringe of the major cities and regional centres is a contestable stage. There are a range of actors who compete in place making processes reshaping the cultural landscape when there is collision over the ownership of space and the dominant narrative. This paper examines the proposition that Sydney’s urban growth has created a zone of conflict on the city’s metropolitan frontier between cultural heritage and the interests of development. In recent years Sydney’s rural-urban fringe has encroached on the village boundaries of Menangle where there has been a collision between the expectation and aspirations of villagers and a local land developer. Village activism has sought to defend a landscape aesthetic created by settler colonialism in the face of neo-liberal capitalist forces intent on re-shaping place. The former enclosed estate village of Menangle, once the province of the Macarthur family on their colonial estate of Camden Park, is being engulfed by the octopus that is Sydney’s urban sprawl. State sponsored urban planning processes have threatened the villagers’ community identity and a sense of place in the name of progress and development. Local government has limited capacity to negotiate in a landscape where a battle over cultural values has produced winners and losers as the colonial frontier did over 200 years ago.