As urbanization increases globally, wildlife species are changing their behaviour in many ways. Urban animals are often bolder, or less fearful of new stimuli, than rural animals. While adaptation can drive behavioural changes in urban animals, other factors, such as learning or habituation, can also lead to behavioural modifications. To determine how repeated exposure to a non-threatening human affects song sparrow (Melospiza melodia) behaviour in urban and rural habitat, we measured boldness as flight initiation distance (FID), for 5 consecutive days. We found that urban birds had consistently lower FID’s than their rural counterparts from days 1–4, yet there was no difference in rural and urban FID by trial 5. FID decreased over 5 days of repeated trials in the rural populations, but not the urban. These results suggest that habituation can occur quickly in rural birds and may account for the greater boldness we typically see in urban populations.