In the 1940s, Aldo Leopold took extensive notes on birds and their sounds near his iconic shack in Baraboo, Wisconsin, USA. His observations, along with his land management techniques, helped frame his seminal book, A Sand County Almanac. After his death, two interstate highways were built near his property and subjected this historically significant area to traffic noise. While highways currently represent vital transportation corridors, their observed and potential impacts on biodiversity and ecosystem services are cause for concern. As the area including Leopold’s shack is now an Important Bird Area, we sought to evaluate the impact of these highways on the bird community and its related acoustic diversity. In 2011, 150 avian point counts were conducted in the three main habitats composing the landscape—upland deciduous forest, floodplain forest, and herbaceous wetland. In 2012, soundscape recordings were collected in seven floodplain forest sites using automated passive acoustic recorders. We described the local bird communities and measured their acoustic diversity. Linear models accounting for additional factors including land cover and vegetation structure characteristics showed that as the distance from highways increased, bird community descriptors (overall abundance and species richness) and acoustic diversity increased (when relationships were significant). On the species level, forest interior specialists were negatively affected by the presence of the highways, contrary to edge specialists. In addition to the direct effects of the edges produced by the highway structure, this difference might be due to the masking effect of traffic noise on interior specialists’ low-frequency vocalizations and their reliance on acoustic, as opposed to visual, communication. We conclude that while habitat structure is a principle driver of bird diversity on a broader scale, highway-induced changes in both habitat structure and soundscapes may affect bird communities.