We examined a 35-year transition in the breeding bird community at a successional study site in a reforesting landscape in southwestern New York, USA. Changes in the successional plot were compared with those in two additional census plots, one in undisturbed forest and the other in a managed tree farm. The territories of 7,429 singing male songbirds were mapped on the census plots. The most dramatic changes in community structure were in the successional plot where total number of territories declined between the beginning of the study (x ¯ = 95.8 territories, 1969–1973) and end of the study (x ¯ = 57.2 territories, 1999–2003); grassland/shrub nesting species were nearly extirpated, and the number of neotropical migrant territories increased from zero in 1969 to 30 in 2003. The average number of neotropical migrant territories in the undisturbed forest plot declined from the beginning of the study (x ¯ = 54.0, 1975–1979) to the end (x ¯ = 44.8, 2003–2007). The average number of territories increased in the managed tree farm from the beginning of the study (x ¯ = 53.6, 1983–1987) to the end (x ¯ = 104.0, 2003–2007) largely due to increases in abundance of temperate zone migrants and resident species. Counts of individual species in the census plots were not highly correlated with counts from regional Breeding Bird Survey routes.