The behavior of adults and young at the time of fledging is one of the least understood aspects of the breeding ecology of birds. Current hypotheses propose that fledging occurs either as a result of parent-offspring conflict or nestling choice. We used video recordings to monitor the behavior of nestling and adult grassland songbirds at the time of fledging. We observed 525 nestlings from 166 nests of 15 bird species nesting in grasslands of Alberta, Canada, and Wisconsin, USA. Overall, 78% of nestlings used terrestrial locomotion for fledging and 22% used wing-assisted locomotion. Species varied in propensity for using wing-assisted locomotion when fledging, with nestling Grasshopper Sparrows (Ammodramus savannarum) and Henslow's Sparrows (Centronyx henslowii) often doing so (47% of fledgings) and nestling Song Sparrows (Melospiza melodia), Common Yellowthroats (Geothlypis trichas), and Chestnut-collared Longspurs (Calcarius ornatus) rarely doing so (3.5% of fledgings). For 390 fledging events at 127 nests, camera placement allowed adults near nests to be observed. Of these, most young fledged (81.5%) when no adult was present at nests. Of 72 fledging events that occurred when an adult was either at or approaching a nest, 49 (68.1%) involved feeding. Of those 49 fledgings, 30 (62.1%) occurred when one or more nestlings jumped or ran from nests to be fed as an adult approached nests. The low probability of nestlings fledging while an adult was at nests, and the tendency of young to jump or run from nests when adults did approach nests with food minimize opportunities for parents to withhold food to motivate nestlings to fledge. These results suggest that the nestling choice hypothesis best explains fledging by nestlings of ground-nesting grassland songbirds, and fledging results in families shifting from being place-based to being mobile and spatially dispersed.