This chapter is concerned with the retrofitting of suburbia, especially the periphery of Toronto, Canada, and the need to develop a more nuanced understanding of the character of suburban landscapes. This chapter challenges the often-dismissive attitudes expressed by urbanists towards suburbia and suburbanites. This is not to say that the ‘suburbs’ are without their problems. Rather, in order to appreciate and attend to the problems within the suburbs this must be done from within, not from afar by intellectual and policy elites who reside within the urban core and who perceive the suburbs as incomplete or immature cities. A more productive outcome can be achieved by listening to and learning from the lived experiences, city-building expertise, and political presence of suburban communities. In essence, this chapter provides a suburban magical mystery tour based upon work with the Greater Toronto Suburban Working Group (GTSWG), a loose collective of ‘thinkers and doers’ that convened over a five-year period from 2010–2015 in the Toronto region as part of a large-scale research agenda on global suburbanisation.