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This article examines the ethnicization of Toronto’s urban landscape and strategies of resistance in Dionne Brand’s novel What We All Long For (2005). Through Brand’s depiction of immigrant families and their Toronto-born children navigating the city’s ethno-racialized geography, it reveals how structural inequalities manifest spatially and explores possibilities for transcending these imposed boundaries. The analysis illustrates that Toronto’s multicultural facade conceals systematic spatial segregation, relegating immigrant populations to ethnicized enclaves characterized by economic disinvestment and constrained social mobility. First-generation immigrants, exemplified by the Vu family’s experience of professional deskilling and Jackie’s parents’ lives in Alexandra Park’s hyperghetto, strategically negotiate these urban conditions to cultivate community and belonging despite systemic marginalization. Their Toronto-born children employ distinct spatial practices, using art installations and graffiti to assert ownership over urban space and form porous communities transcending ethnic boundaries. While immigrant parents accommodate the city’s ethnicizing logic to secure belonging within prescribed spatial parameters, the second generation radically reimagines urban space through creative interventions that resist essentialization. This generational analysis demonstrates how both groups contribute to Toronto’s cosmopolitan transformation through complementary spatial strategies, challenging reductive narratives of immigrant assimilation while illuminating the complex dynamics of belonging, exclusion, and resistance in contemporary urban Canada.