Mercury (Hg) loading and methylation in aquatic systems causes a variety of deleterious effects for fish and wildlife populations. Relatively little research has focused on Hg movement into riparian food webs and how this is modulated by habitat characteristics. This study characterized differences in Hg exposure in aquatic invertebrates and riparian songbirds across a large portion of the Willamette River system in western Oregon, starting at a Hg-contaminated Superfund site in the headwaters (Black Butte Hg Mine) and including a reservoir known to methylate Hg (Cottage Grove Reservoir), all downstream reaches (Coast Fork and Willamette River) and off-channel wetland complexes (Willamette Valley National Wildlife Refuge Complex). After accounting for year, date, and site differences in a mixed effects model, MeHg concentrations in aquatic invertebrates varied spatially among habitat categories and invertebrate orders. Similarly, THg in songbird blood varied by among habitat categories and bird species. The highest Hg concentrations occurred near the Hg mine, but Hg did not decline linearly with distance from the source of contamination. Birds were consistently elevated in Hg in habitats commonly associated with enhanced MeHg production, such as backwater or wetlands. We found a positive but weak correlation between aquatic invertebrate MeHg concentrations and songbird THg concentrations on a site-specific basis. Our findings suggest that Hg risk to riparian songbirds can extend beyond point-source contaminated areas, highlighting the importance of assessing exposure in surrounding habitats where methylmercury production may be elevated, such as reservoirs and wetlands.