ObjectiveOne large focus of personality psychology is to understand the biopsychosocial factors responsible for adult personality development and well‐being change. However, little is known about how macro‐level contextual factors, such as rurality–urbanicity, are related to personality development and well‐being change.MethodThe present study uses data from two large longitudinal studies of U.S. Americans (MIDUS, HRS) to examine whether there are rural–urban differences in levels and changes in the Big Five personality traits and well‐being (i.e., psychological well‐being, and life satisfaction) in adulthood.ResultsMultilevel models showed that Americans who lived in more rural areas tended to have lower levels of openness, conscientiousness, and psychological well‐being, and higher levels of neuroticism. With the exception of psychological well‐being (which replicated across MIDUS and HRS), rural–urban differences in personality traits were only evident in the HRS sample. The effect of neuroticism was fully robust to the inclusion of socio‐demographic and social network covariates, but other effects were partially robust (i.e., conscientiousness and openness) or were not robust at all (i.e., psychological well‐being). In both samples, there were no rural–urban differences in Big Five or well‐being change.ConclusionsWe discuss the implications of these findings for personality and rural health research.