Through uneven processes of planning by a multiplicity of participants, Edinburgh’s built environment continues to emerge as the product of many competing strategies and projects of development. The 2005 proposal of a dramatic new development intended for an area of the city’s Old Town represents one such project in which many powerful municipal and commercial institutions are invested. As one of the last remaining residential areas of the Old Town, the population of which has experienced in recent decades a gradual transformation towards transience, the Canongate became the focus of a heated campaign organised by remaining residents who sought to claim their rights to participation in the redevelopment of their neighbourhood. This thesis explores the efforts of these campaigners to accomplish a Deleuzian reterritorialisation of the Canongate, in the face of perceived threats to its community, territorial identity and built environment, represented by the development proposal named Caltongate. The remarkable success of the campaign in cultivating a sense of community belonging and mobilising residents in collaborative efforts at reimagining alternative futures for the Canongate was ultimately unable to affect Caltongate’s approval through formalised bureaucratic procedures. Through an innovative programme of community research and representation, however, the campaigners have impacted subsequent community-led planning efforts throughout the Old Town, which emphasise small-scale development that is accountable to both the residential community and the built heritage of the Old Town. The relationship between the Canongate neighbourhood and the proposed Caltongate development, which is currently suspended in the depressed economic climate, emerges in this thesis as mutually constructive, as well as principally opposed.