Flights over open water can be challenging for migrating songbirds. Despite numerous observations of songbirds migrating over remote islands, virtually nothing is known about the proportion of songbirds risking to fly offshore rather than to follow the coastline. By means of large-scale automated radio-telemetry, we individually tracked songbirds during their autumn migration through the German Bight area in the south-eastern North Sea. Our tracking network facilitated the recording of movement patterns over the bay and, for the first time, the estimation of the proportions of individuals embarking on offshore flights from their coastal stopover sites. Our data are consistent with previous observations of decreasing migration densities from nearshore to offshore, i.e. from east to west in autumn. Still, we revealed a considerable proportion of 25% of birds flying offshore. The tendency to fly offshore decreased from west to south migrants, which is in line with optimal bird migration theory. Among south-west migrating species, which also comprise the vast majority of songbird species migrating through the German Bight area, thrushes showed the highest proportions of offshore flights. Considering the recent and ongoing increase of artificial offshore structures, our results suggest that some species or species groups might especially face an increased risk of being negatively affected.