Like many resources in the Chesapeake Bay region of the U.S., many waterbird nesting populations have suffered over the past three to four decades. In this study, historic information for the entire Bay and recent results from the Tangier Sound region were evaluated to illustrate patterns of island erosion and habitat loss for 19 breeding species of waterbirds. Aerial imagery and field data collected in the nesting season were the primary sources of data. From 1993/1994 to 2007/2008, a group of 15 islands in Tangier Sound, Virginia were reduced by 21% in area, as most of their small dunes and associated vegetation and forest cover were lost to increased washovers. Concurrently, nesting American black ducks (Anas rubripes) declined by 66% , wading birds (herons-egrets) by 51%, gulls by 72%, common terns (Sterna hirundo) by 96% and black skimmers (Rynchops niger) by about 70% in this complex. The declines noted at the larger Bay-wide scale suggest that this study area maybe symptomatic of a systemic limitation of nesting habitat for these species. The island losses noted in the Chesapeake have also been noted in other Atlantic U.S. coastal states. Stabilization and/or restoration of at least some of the rapidly eroding islands at key coastal areas are critical to help sustain waterbird communities.