The Painted Bunting (Passerina cirus) is a small (~16g), short/medium-distance migratory songbird that is listed as a species of conservation concern by the US Fish and Wildlife Service. Painted Buntings breed in two distinct populations, one eastern population and one interior population, separated by a 500 km gap that stretches from Mississippi to Georgia. I analyzed tracking data from 112 Painted Buntings from 11 different breeding sites to explore how individuals from different breeding sites differ in wintering location (chapter 2) and migratory timing (chapter 3). Additionally, I examined differences in migratory behavior between male and females in the eastern population (chapter 4). My results reveal that eastern and interior Painted Buntings remain separate throughout the annual cycle. Within each population, individuals from different regions of each population mix extensively on the non-breeding ground. Migratory timing was drastically different between the two populations, with interior Painted Buntings departing the breeding ground two months prior to birds from the eastern population. In eastern Painted Buntings, some variation in fall departure could be attributed to differences in vegetation greenness and temperature, suggesting that eastern birds may adjust their fall departure from year to year in accordance with yearly variation in environmental conditions. Fall departure was not closely linked to environmental conditions in the interior population. I found that eastern Painted Buntings arrive on the breeding ground at approximately the same time each year, suggesting that spring arrival timing may have a strong instinctual component. In eastern Painted Buntings, males arrived on the breeding ground before females, but I found no differences in fall departure timing between the sexes. In the eastern population, females wintered slightly farther north on average than males. This work demonstrates the considerable differences in migratory behavior that are possible within a single species.