Estimating the abundance and breeding success of territorial songbirds is challenging. Various types of surveys and analyses are available, but all receive some criticism in the literature, and most methods are rarely compared with results obtained using intensive monitoring efforts. We assessed the efficacy of transect and point‐count surveys to estimate the abundance of male Bobolinks (Dolichonyx oryzivorus) and detect evidence of nesting and fledging by comparing the results of those surveys to results from more intensive monitoring (i.e., spot mapping and nest monitoring). We monitored 36 fields (254 ha) of late‐harvest hay, restored grassland, and fallow fields in the Luther Marsh Wildlife Management Area and on four farms in southern Ontario, Canada, in 2018. Compared to the number of territories identified based on spot mapping (197), distance sampling analysis of transect survey data provided a more accurate estimate of the abundance of male Bobolinks (230, 95% CI: 187, 282) than N‐mixture models of transect (668, 95% CI: 332, 1342) and point‐count (337, 95% CI: 203, 559) data. Three visits to survey transects and five to point counts did not effectively detect evidence of Bobolink breeding (i.e., nesting or fledging) in fields compared to spot mapping and nest monitoring. Distance sampling analysis of transect data appears promising for estimating the number of Bobolink territories in an area, e.g., those impacted by conservation programs. If estimates of the number of nesting Bobolinks and frequency of fledging are of interest, spot mapping and nest monitoring could be implemented at a subset of sampled fields. Our results suggest that additional studies to evaluate model‐based estimates of abundance with the best available information (e.g., from spot mapping of marked or unmarked populations and nest monitoring) would be useful to ensure that robust estimates are provided to support population estimates and conservation actions.