The literature on the transition to postmodernism, postfordism and participatory planning stresses the value of the economic and planning process shifts that have occurred in the late 1960s and early 1970s. This paper compares two periods of planning and urban development in Toronto: one running from 1959 to 1962, at the height of modernism, fordism and expert‐driven planning, and the other, from 1989 to 1992, set within the postmodern, postfordist and participatory planning era. In line with expectations arising from the literature, the study reveals stark distinctions between the two periods. It documents the breaking up of the modern consensus around the progress ideology into a postmodern constellation of values. As a result, the range of issues debated on the planning scene was much broader over the second period than over the first. Overall, however, results point to a mixture of continuity and change between the two periods and thus diverge from this literature’s strong emphasis on transition. Contrary to expectations, citizen mobilization was pervasive in both periods, although there were major differences in the nature of activism and in the issues that were raised. Over the first period most activism originated from ratepayer organizations dedicated to the protection of single‐family‐home neighbourhoods from encroachments, whereas the second period featured, along with such associations, advocacy groups championing environmental and social causes. The two periods are also distinguished by different planning implementation capacities. Whereas in the first period, planning had the means to implement its visions, this was no longer the case in the second period. In the late 1980s and early 1990s, planning was thus incapable of aligning urban development with its environmental and social ideals, which meant that, by default, planning practice over the second period proceeded pretty much according to land‐use and transportation principles evolved in the early postwar decades. In sum, distinctions between the two periods were far more evident in the discourse than in the implementation sphere.