Beaches and islands provide economic value to humans and critical habitat for breeding and foraging wildlife. These ecosystems, however, are being severely impacted by global climate change and sea level rise through increased erosion and frequency of inundation. The case study presented here aimed to document island loss in the Chesapeake Bay and Delmarva coastal bay region of the United States using image processing techniques within a GIS from 1986 to 2016. Satellite imagery from Landsat Thematic Mapper (TM) and Operational Land Imager (OLI) sensors were processed within ArcMap 10.5 to determine spatial and temporal trends in island and beach habitat. Calculation of unweighted Cohen’s Kappa showed that classified scenes were, on average, within the range of moderate agreement between the classified Landsat scenes and the validation imagery within Google Earth (0.539). Recommendations regarding existing beach habitat management and future supplementation were created based on these results. From 1986 to 2016, island area declined by over 1,200 hectares (ha) with agriculture/open field (all open vegetated spaces) declining by nearly 82% and beach, surprisingly, increasing nearly 2%. This study was the first to document Chesapeake Bay region-wide island loss beyond the mid-2000s. The accuracy of this study was limited slightly by the 30 m spatial resolution of the imagery used. This technique may be best suited for documenting trends on large islands and along the mainland coastline.