The author explores the problem of territorial reorganization of the metropolitan area within the Canadian evolutionary federal system, taking as an example the cities of Toronto and Montreal. The results of the research indicate that adaptation strategies, applied by states aiming at empowering the metropolis, depend on the general level of the territorial units’ autonomy. The existence of strong local self-government favours creation of intercommunal cooperation structures without dissolution of current local territorial units. Territorial reorganization in the case of states with a low level of local autonomy may facilitate elimination of former local units by theirs amalgamation in new, larger metropolitan self-government structures. As far as this context is concerned, Canada constitutes a very interesting study case. Taking into consideration Canadian evolutionary federal system, highly limited local autonomy of the cities, and its mix of European and American traditions, one can observe almost all the above-mentioned dimensions of reform and adaptation strategies. Advanced and institutionalized intercommunal cooperation, developed in Toronto and Montreal in the middle of the 20th century, was interrupted by amalgamation imposed by provincial government, which resulted in creation of new, enlarged metropolitan cities of Toronto in 1998 and Montreal in 2002. In both cases the amalgamation has not been accepted by a part of the population and destabilized cooperation in these metropolitan areas. The trouble with amalgamation led to abandonment of further structural and territorial reforms, which were replaced by functional ones, taking the form of special agreements between Toronto and Montreal and their respective provinces (Ontario and Quebec), giving them both new competences and financial resources. Regardless of any difficulties in pursuing an appropriate metropolitan regime and the suitable position for the metropolis in the structure of a political and territorial system, both cities have achieved strong economic performance and high quality of life.