In this study, we examined trajectories of Big Five personality development in the five years before and after retirement. Our sample was composed of 690 retirees (ages 51-81) and a propensity-score matched comparison group of 532 non-retirees drawn from a nationally representative longitudinal study of the Netherlands. Participants contributed data across a maximum of six measurement waves over a period of seven years. In the month after retirement, participants experienced sudden increases in openness and agreeableness followed by gradual declines in these traits over the next five years. Emotional stability increased before and after retirement. The transition to retirement was not associated with changes in conscientiousness or extraversion. Further, we found significant individual differences in development across the transition to retirement for each personality trait but could not identify any moderators that accounted for these individual differences. These results contribute to our understanding of personality development in older adulthood as well as the temporal dynamics of personality change in response to major life events.