Many studies have demonstrated the importance of early successional forest habitat for breeding bird abundance, composition, and diversity. However, very few studies directly link measures of bird diversity, composition and abundance to measures of forest composition and structure and their dynamic change over early succession. This study examines the relationships between breeding bird community composition and forest structure in regenerating broadleaf forests of southern New England, USA, separating the influences of ecological succession from retained stand structure. We conducted bird point counts and vegetation surveys across a chronosequence of forest stands, that originated between 2 and 24 years previously in shelterwood timber harvests, a silvicultural method of regenerating oak-mixed broadleaf forests. We distinguish between vegetation variables that relate to condition of forest regeneration and those that reflect legacy stand structure. Using principal components analyses we confirmed the distinction between regeneration and legacy vegetation variables. We ran regression analysis to test for relationships between bird community variables, including nesting and foraging functional guild abundances, and vegetation variables. We confirmed these relationships with hierarchical partitioning. Our results demonstrate that regenerating and legacy vegetation correlate with bird community variables across stand phases, and that the strength with which they drive bird community composition changes with forest succession. While measures of regeneration condition explain bird abundance and diversity variables during late initiation, legacy stand structure explains them during stem exclusion. Canopy cover, ground-story diversity, and canopy structure diversity are the most powerful and consistent explanatory variables. Our results suggest that leaving varied legacy stand structure to promote habitat heterogeneity in shelterwood harvests contributes to greater bird community diversity. Interestingly, this is particularly important during the structurally depauperate phase of stem exclusion of young regenerating forests.