Long-term population trends are considerable sources of information to set wildlife conservation priorities and to evaluate the performance of management actions. In addition, trends observed in functional groups (e.g., trophic guilds) can provide the foundation to test specific hypotheses about the drivers of the observed population dynamics. The aims of this study were to assess population trends of breeding birds in Lombardy (N Italy) from 1992 to 2019 and to explore the relationships between trends and species sharing similar ecological and life history traits. Trends were quantified and tested for significance by weighted linear regression models and using yearly population indices (median and 95% confidence interval) predicted through generalized additive models. Results showed that 45% of the species increased, 24% decreased, and 31% showed non-significant trends. Life history traits analyses revealed a general decrease of migrants, of species with short incubation period and of species with high annual fecundity. Ecological traits analyses showed that plant-eaters and species feeding on invertebrates, farmland birds, and ground-nesters declined, while woodland birds increased. Further studies should focus on investigation of the relationship between long-term trends and species traits at large spatial scales, and on quantifying the effects of specific drivers across multiple functional groups.