AbstractSpecies exploiting seasonal environments must alter timings of key life‐history events in response to large‐scale climatic changes in order to maintain trophic synchrony with required resources. Yet, substantial among‐species variation in long‐term phenological changes has been observed. Advancing from simply describing such variation towards predicting future phenological responses requires studies that rigorously quantify and explain variation in the direction and magnitude of changing timings across diverse species in relation to key ecological and life‐history variables. Accordingly, we fitted multi‐quantile regressions to 59 years of multi‐species data on spring and autumn bird migration timings through northern Scotland. We demonstrate substantial variation in changes in timings among 72 species, and tested whether such variation can be explained by species ecology, life‐history and changes in local abundance. Consistent with predictions, species that advanced their migration timing in one or both seasons had more seasonally restricted diet types, fewer suitable breeding habitat types, shorter generation lengths and capability to produce multiple offspring broods per year. In contrast, species with less seasonally restricted diet types and that produce single annual offspring broods, showed no change. Meanwhile, contrary to prediction, long‐distance and short‐distance migrants advanced migration timings similarly. Changes in migration timing also varied with changes in local migratory abundance, such that species with increasing seasonal abundance apparently altered their migration timing, whilst species with decreasing abundance did not. Such patterns broadly concur with expectation given adaptive changes in migration timing. However, we demonstrate that similar patterns can be generated by numerical sampling given changing local abundances. Any apparent phenology‐abundance relationships should, therefore, be carefully validated and interpreted. Overall, our results show that migrant bird species with differing ecologies and life‐histories showed systematically differing phenological changes over six decades contextualised by large‐scale environmental changes, potentially facilitating future predictions and altering temporal dynamics of seasonal species co‐occurrences.