Given the difficulty of following free-living, dispersing juvenile songbirds, relatively little is known about when, where, how, and from whom these young birds learn their songs. To explore these issues, we studied the Chipping Sparrow (Spizella passerina), males of which have a single, simple song, but populations of which may contain 20–30 different songs. In our western Massachusetts study sites, we color-banded 324 nestling and 32 fledgling sparrows. Twelve of these banded males returned to our study areas, dispersing a few hundred meters to 1.8 km away from their natal territories. The song of each yearling closely matched only one of his immediate neighbors on the breeding territory, revealing that a yearling sparrow precisely imitates one of his close neighbors after dispersal. Evidence from this field study and a previous laboratory study show that a young male is able to learn songs either during his hatching year or the following spring, perhaps depending on his chances of song exposure or social interaction with territorial neighbors.