The urban environment poses novel anthropogenic challenges to wildlife. Some species have been noted for changes in their behavior in response to humans and urban-associated activities. Understanding the anthropogenic factors which influence these behavioral changes would contribute significantly to avian conservation in an increasingly urbanized world. We investigated the flight initiation distances (FIDs) and alert distances (ADs) of wild Song Sparrows (Melospiza melodia) and Northern Cardinals (Cardinalis cardinalis) in urban and rural habitats of southwestern Virginia to determine if wild songbirds' tolerances for human approaches differed by species or habitat type (urban or rural). We found Song Sparrows to be more tolerant than Northern Cardinals of human approaches, and urban birds of both species tended to tolerate closer approaches than did rural birds. We then investigated whether cues such as gaze direction or human figure explain differences in Song Sparrows' approach response behaviors. We found urban Song Sparrows' FIDs to be significantly shorter than rural birds' FIDs in response to treatments using a human approach for both direct and concealed gazes. However, no significant habitat differences were detected in response to the non-human approach treatments using umbrellas with and without eyespots. Our findings demonstrate risk-tolerance behaviors like AD and FID to vary greatly between species, habitats, and characteristics of the approach.