Aims: The aims of this study were to examine trajectories of headache in relation to retirement and to clarify the role of work stress and stress-prone personality. Methods: Headache prevalence during the 7 years before and after retirement was measured by annual questionnaires from GAZEL cohort comprising French national gas and electricity company employees (n = 12,913). Odds ratios and 95% confidence intervals for headache during pre- peri- and post-retirement were calculated. The role of effect modifiers (work stress, type A or hostile personality) was tested by multiplicative interactions and synergy indices. Results: An 11-13% reduction in headache prevalence was found during pre- and post-retirement, whereas decline was much steeper (46%) during the retirement transition. In absolute terms, the decline was greater among persons with high work stress or stress-prone personality than among other participants. Conclusions: Retirement is associated with a decrease in headache prevalence, particularly among persons with a high amount of work stress or proneness to over-react to stress.