Point Pelee National Park of Canada in southwestern Ontario, an important migratory route and vital breeding area for many birds, has localized areas of organochlorine (OC) pesticide contamination from agricultural production during the 1950s and 1960s. During 2001 and 2002, we investigated movement of persistent contaminants through the food web with the insectivorous tree swallow (Tachycineta bicolor) as a sentinel. The a priori site classifications, contaminated or reference, were based on soil residues of dichlorodiphenyltrichloroethane (DDT) and its breakdown products (sigmaDDT), dieldrin, and other OC pesticides. In 2001, all nestling tissue samples were pooled by site, and residue levels did not reflect the soil contaminant status. To improve sampling accuracy in 2002, tissue residues were determined from birds in individual nests. This showed OC pesticides to be higher in samples from contaminated sites compared with reference sites (p = 0.031). Polychlorinated biphenyls (PCBs), which were not detected in soil samples, were present in the nestlings and were not related to site of origin (p = 0.422). In 2002, dietary samples were collected from nestlings and identified to taxon, and representative insects collected from nesting sites were analyzed for PCBs and other OCs. Consumption of terrestrial prey was positively correlated with tissue residues of sigmaDDT (p = 0.006), whereas PCBs came from aquatic prey, Hexagenia mayflies (p = 0.003). Dietary details proved valuable in this study of contaminant transfer in insectivorous vertebrates.