Colinus virginianus (Northern Bobwhite) populations showed signs of decline beginning in the early 1900s and are part of a growing list of wildlife species dependent on early successional habitat whose populations are suffering similar fates. Among the numerous factors that contributed to these range-wide declines, most significant are habitat loss and fragmentation due to changes in land use and land cover. In an effort to document landscape composition and cover-type changes, we mapped and analyzed landscape features along 7 breeding bird survey routes on Maryland's Eastern Shore in 2 different years spaced 55 years apart, 1964 and 2019. We calculated total patch area and conducted a randomization test for paired study design to test for differences in land cover after 55 years between the 5 landscape attributes that influence populations dependent on early successional vegetation within an agriculture-dominated landscape. The 5 landscape attributes were agriculture, forest cover, hedgerow length, early successional habitat, and development. In the 55-year span, agricultural land declined from 58.4% to 48.8% and had the largest change in cover area across the 5 landscape attributes. Developed land increased from 7.5% to 12.2%, while forested land remained the same at 24.4%.