Changes in the coverage of trees and shrubs on the North Dakota landscape since Euro-American settlement have likely had a pronounced impact on bird species that favor woody vegetation. Long-term data sets on breeding bird populations in wooded habitats in North Dakota or in the Great Plains are scarce. In 1975 a wildlife habitat plot was established in a 10.5 ha cropland field with a long history of small-grain production. The objective of this article is to evaluate the successional changes in bird populations as the habitat at this site became more biologically and structurally complex after the establishment of a diverse stand of shrubs and trees. Between 1975 and 2015, 103 species or varieties of native and non-native trees, shrubs, or vines were planted in this wildlife habitat plot (hereafter woodlot); 58.2% of those species were still present in 2016. The avian community in the woodlot increased in abundance and diversity as the woody vegetation increased in complexity and maturity, but the changes in abundance varied among ecological bird groups. Grassland bird abundance remained relatively constant but uncommon throughout the four decades after woody vegetation was first established. Bird species associated with shrublands and open woodlands and edges responded positively and showed the greatest increases in abundance during the 41-year period. The abundance of bird species associated with open areas with scattered trees or shrubs (i.e., savanna habitat) increased during the first half of the study but declined during the second half. Bird species associated with forest habitats were rare throughout the 41-year period, but their abundance increased during the most recent two decades. Results of this study are important for informing decisions about restoration efforts of riparian forests and other native wooded areas in the Great Plains and setting expectations for the time-scale required for the return of assemblages of species of woodland birds.