Exposure to multiple classes of contaminants, both legacy and those of emerging concern (CECs), were assessed in tree swallow (Tachycineta bicolor) tissue and diet samples from 6 sites along the Maumee River, OH to understand both exposure and possible effects of exposure to those CECs for which there is little avian data. The six sites represented a gradient from intensive agriculture upstream to highly urbanized and industrial landscapes downstream; 1 – 2 remote Wisconsin lakes were assessed for comparative purposes. Cytochrome P450 induction, DNA damage, and thyroid function were also assessed relative to contaminant exposure. Bioaccumulative CECs, such as polybrominated diphenyl ethers (PBDEs) and perfluorinated substances, did not follow any upstream to downstream gradient, but both had significantly greater concentrations along the Maumee River than at the remote lake sites. Greater exposure to PBDEs was apparent in swallows at or near wastewater treatment facilities than at other sites. Total polychlorinated biphenyl and total polycyclic aromatic hydrocarbon concentrations were at greater concentrations in swallows at downstream locations compared to upstream sites and were associated with higher ethoxyresorufin-O-dealkylase activity. Few herbicides or non-organochlorine insecticides were detected in swallow tissues or their food, except for atrazine and its metabolite desethylatrazine, the latter of which was detected in all food samples, eggs, and nearly all nestling carcasses from along the Maumee River. Few pharmaceuticals and personal care products were detected in tree swallow tissue or sediment samples except for DEET and iopamidol. Both were detected in most liver samples, but not in eggs, and were detected at the remote lake sites as well. This is one of the most comprehensive assessments to date of exposure and effects of CECs in birds.