Differences in habitat characteristics experienced during rearing associate with variation in a range of behavioral phenotypes such as exploratory behavior, foraging behavior and food preference. The habitat-dependent selection hypothesis predicts that animals develop behavioral characteristics fitted to their rearing environment. Yet, little is known about how habitat characteristics during rearing shape how animals face winter conditions and adjust their winter foraging behavior. The aim of this study was to explore how fine-scale rearing habitat characteristics associate with exploratory behavior, food selection and foraging performance during winter. For this, we measured habitat characteristics during the breeding season in territories of wild great tits (Parus major), and tested first-year juvenile birds that fledged from these territories for exploratory and foraging behavior at feeders during winter. We found evidence that faster explorers were raised in territories with lower quality-related habitat characteristics. In addition, fast exploring fledglings visited the feeders significantly more (total visits). Moreover, the rearing environment, via caterpillar availability and tree species composition, determined diet selection during winter in first year birds. These results show support for the habitat-dependent selection hypothesis, since exploratory behavior as well as food preferences during winter associate with habitat features of the rearing territories during development. This pattern can be caused either by the kinds of foods prevalent at these sites or because of intrinsic individual differences. Further experiments are needed to disentangle these two.