Migratory behavior can be an important factor in determining contaminant exposure in avian populations. Accumulation of organochlorine (OC) pesticides while birds are wintering in tropical regions has been cited often as the reason for high concentrations in migrant populations. To explore this issue, we satellite tracked 16 Ospreys (Pandion haliaetus) over the period 1996–2003 from breeding sites in British Columbia, Canada, and integrated the results into a database on 15 Ospreys that were satellite tracked over the period 1995–1999, from breeding locations in Washington and Oregon, USA. Data on wintering sites of 31 Ospreys in Mexico and Central America were used for spatially targeted sampling of prey fish. Concentrations of the main organochlorine contaminant, p,p′-dichloro-diphenyl-dichloroethylene (DDE), in fish composites from Mexico ranged from 0.005 to 0.115 μg/g wet mass. Significant differences existed among fish families in p,p′-DDE, total dichloro-diphenyl-trichloroethane (ΣDDT), Σchlordanes, and total polychlorinated biphenyls (ΣPCBs). Catfish (family Ariidae) generally had significantly higher levels of DDT metabolites and other organochlorine contaminants compared to other fish families collected. Differences in prey contaminant levels were detected among the collection sites around coastal Mexico, with fish from Veracruz State generally having higher levels of DDT metabolites, Σchlordanes, ΣPCBs, and hexachlorobenzene. Eggs collected from 16 nests throughout the Pacific Northwest (nine from British Columbia, seven from Oregon and Washington) where Ospreys had been satellite tagged, showed marked variation in levels of DDT metabolites (p,p′-DDE; range 0.02–10.14 μg/g). Wintering site had no significant effect on contaminant concentrations in sample eggs from those specific Ospreys; rather concentrations of p,p′-DDE, were predicted by breeding sites with highest levels in eggs of Ospreys breeding in the lower Columbia River, consistent with published reports of continued high concentrations of DDT and related compounds in that system.