Aim In the Northern Hemisphere, bird migration from the tropic to the temperate zone in spring is thought to proceed at a rate determined in large part by local phenology. In contrast, little is understood about where birds go or the factors that determine why they move or where they stop during the post-breeding period. Location Study sites were in Oregon, Nebraska and Vermont, and location data we collected extend south to Argentina. Methods We deployed light-level geolocators on individual Bobolinks from three populations across the breeding range and compare their southbound movement phenology to austral greening as indicated by the Normalized Difference Vegetation Index. Results Bobolinks from all breeding populations synchronously arrived and remained for up to several weeks in two sequential, small non-breeding areas that were separated by thousands of kilometres, before staging for pre-alternate moult. Similar to the migration patterns of birds to northern breeding areas, movements into the Southern Hemisphere corresponded to increasing primary productivity. Main conclusions Our findings suggest that the Bobolink’s southbound migration is broadly constrained by resource availability, and its non-breeding distribution has been shaped by the seasonal phenology of grasslands in both time and space. This is the first documentation of individual birds from across a continental breeding range exhibiting phenological matching during their post-breeding southward migration. Known conservation threats overlap temporally and spatially with large concentrations of Bobolinks, and should be closely examined. We emphasize the need to consider how individuals move and interact with their environment throughout their annual cycle and over hemispheric scales.