In North America, roughly three-quarters of grassland bird species have experienced population declines since 1970. These declines have a variety of causes, but the degradation, fragmentation, and outright loss of natural habitat stand out among them. As a result of this habitat loss, many grassland birds now rely on farm fields for nesting territory. This often results in the destruction of nests and young birds by combines or mowers, as many crops are harvested during peak breeding season for birds. Combating this crisis requires conservationists to work closely with farmers and landowners to find solutions that work for them as well as the birds that depend on their land. Understanding how birds respond to different crops and management regimes can inform conservation decisions on a regional level. Pennsylvania’s Chester County is an ideal area to study these dynamics as it has historically had an agricultural economic base but has seen losses in overall farmland resulting from population growth and economic diversification. This study used point count bird surveys, conducted from May 9 to July 16, 2022, across 21 fields in Chester County to assess nesting habitat suitability for three ground nesting grassland birds: Bobolinks (Dolichonyx oryzivorus), Eastern Meadowlarks (Sturnella magna), and Grasshopper Sparrows (Ammodramus savannarum). Fields were categorized into four groups: hayfields mowed before June 1, hayfields mowed after July 1, wheatfields, and row crop fields (corn or soybeans). The data collected in this study show that Bobolinks had a strong preference for hayfields mowed after the end of June, while Grasshopper Sparrows preferred hayfields that were mowed before June. Eastern Meadowlarks occurred in both early cut and late cut hayfields in roughly equal numbers. All three species showed a strong preference for hayfields over the other crops surveyed, although more data may be needed to further assess whether there may be underappreciated value amongst the non-hay crops. Additionally, all three species exhibited edge avoidance, favoring field interiors.