Postcolonial urban isolation is experienced by people in postcolonial cities and is characterized by marginalization and dislocation, and this is usually a consequence of historical, social and cultural turmoil. The city is not only a physical space, but also a cultural and political space in the context of postcolonialism, where the former colonial territories struggle against the traces of imperialism. As individuals with different cultural backgrounds relocate to these urban centers, they are often confronted by alienation, in the way they are socially positioned as well as in their efforts to be assimilated into the prevailing cultural discourses. Systemic inequalities, racism and the legacies of colonial systems add to this isolation which persists up until now. Within such surroundings, people might end up being torn between all identities, as they become confused with having to move in between the past experience of the colonial rule and the present life in an urban setting. The postcolonial city, thus, turns into a symbol of disrupted belongingness, where isolation is not only about a personal issue but it is also a shared state of affairs, which is caused by the complications of migration, displacement and uneven spread of power in the postcolonial societies. The symbolism and the literal landscape of alienation, dislocation and postcolonial trauma are critically explored to depict the urban Canada and Toronto in particular in The Question by Austin Clarke (1999). The novel anticipates the problem of the invisibility of race, divided identity, as well as physical marginalisation of space and diasporic rootlessness. These features show the complex interrelationship between the geographic location of the city and the psychological interior of a main character who is a Caribbean immigrant and addresses the issue of social erasure. Rather than the multicultural belonging ideal, the account given by Clarke reveals us the ugly faces and exclusions that lurk beneath the much-billed Canadian diversity. The article asserts using the postcolonial and spatial theory that Toronto is not multicultural utopia but rather a world of colonial violence. The city and its very shape and tone, the chilled nature of the streets and the impersonalism of the institutions, the cultural unresponsiveness to the immigrants of the Black world, all become allegorically the landscapes of exile. Depending on the theoretical assumptions of Edward Said, Homi Bhabba, Rinaldo Walcott, and Katherine McKittrick, the analysis has shown how the city world seems to the protagonist of Clarke as a product of building and symbolical threat. This paper examiknes how the author Austin Clarke depicts urban Canada and Toronto to be or symbolise alienation and postcolonial trauma in the question. The city of Toronto, which has been romanticised as a diversity paradise, is depicted in the novel by Clarke as a polarised continent; the black Caribbean migrants are challenged with cultural alienation, and institutional obliteration. This disrupted urban subject experience of the protagonist is revealed with the help of literary and spatial theory expressed on the medium of this paper with its further application to the theme of diasporic subjectivity.