Wintering birds serve as vital climate sentinels, yet they are often underrepresented in comprehensive surveys and overlooked in studies of avian diversity change. Here, we provide a continental-scale characterization of change in multiple facets of wintering avifauna and examine the effects of climate change on these dynamics. We reveal a strong functional reorganization of wintering bird communities marked by a distinct east-west gradient in functional diversity change, along with a superimposed north-south gradient in trait composition change. Assemblages in the eastern US saw an expansion of the functional space and increases in functional originality, evenness, and divergence, while the western US saw contractions of the functional space. Shifts in functional diversity were underlined by significant reshuffling in trait composition, particularly pronounced in the northern US. Finally, we find strong contributions of climate change to this functional reorganization, underscoring the importance of wintering birds in tracking climate change impacts on biodiversity.