Introduction. Prior studies demonstrating age-related declines in headache prevalence have not accounted for the potentially confounding effects of cognitive impairment. Our primary goal was to assess the relationship between aging and self-reported monthly headache days across the cognitive spectrum. Methods. A detailed headache questionnaire was included prospectively as part of an annual mailing to participants in the Sanders-Brown Center on Aging longitudinal cohort. Results. The overall survey response rate was 58.6%, yielding a cohort of 332 cognitively normal, 71 mild cognitive impairment (median Mini-Mental Status Examination [MMSE] score = 27, interquartile range [IQR] = 25-28), and 51 demented (median MMSE score = 24, IQR = 19-26) individuals. Current headaches were reported by 22.8%, 25%, and 27.1%, respectively, across normal, mild cognitive impairment, and dementia subgroups. A negative correlation was observed between age and average headache days in cognitively normal (rho = -0.163, 95% confidence interval [CI] = -0.246 to -0.022, P = 0.004), mild cognitive impairment (rho = -0.255, 95% CI = -0.274 to 0.229, P = 0.0475), and dementia groups (rho = -0.295, 95% CI = -0.457 to 0.159, P = 0.068). Ordinary least-squares regression with backward selection identified age alone, but not gender or MMSE, as predicting headache days in the overall cohort. Conclusions. Aging is associated with a decline in headache days in the absence of any confounding cognitive pathology and is weakly predictive of headache days across the cognitive spectrum. Whether this represents a reporting bias due to dementia or has neurobiological significance warrants further investigation.