The Canada Warbler (Cardellina canadensis) is a species of high conservation importance because of its low overall density and long-term widespread population declines on the breeding grounds. Results of previous research on the species suggest that its breeding habitat preferences vary across its range. However, the underlying processes associated with habitat use are unknown. Using a 20 yr dataset, we developed occupancy models for Canada Warblers to determine the influence of habitat characteristics (e.g., understory vegetation, canopy cover), landscape context (e.g., edge, forest patch size), and species co-occurrence on occupancy, colonization, and local extinction parameters. Our results show that multiple habitats are used by Canada Warblers on the breeding grounds; common variables associated with large-scale, long-term occupancy dynamics are forest age, landscape composition at the 100 m and 500 m scales, and mean patch size. Overall, Canada Warblers were nearly twice as persistent in mature forest stands (>80 yr) and large, mixed forest stands. Further, models indicated that species co-occurrence was an important predictor of Canada Warbler occupancy in some cover types. The results of this study increase our understanding of population processes over large, dynamic landscapes and provide essential conservation information to improve habitat and landscape management for the Canada Warbler.