The Chesapeake Bay is the largest estuary in the United States, and was once one of its most productive. Historically, the Chesapeake supported thousands of migrant and resident species, including oysters, blue crab, shad, herring, and water-fowl. Today the estuary’s productivity is a shadow of what it once was. In 1880, for example, the oyster harvest was 120 million pounds, but this declined to a mere 3 million pounds by 2000—and that actually represented an increase from a historic low in 1993. While the native Chesapeake oyster has fallen victim to disease, a major contributing factor to its decline, along with the health of the estuary, has been the loss of habitat from dredging, sediment loading, and increased pollutant levels. Nearly all of the sediment and pollution originates from human activity on the land surface of the Chesapeake’s watershed (Figure 1). As population and development continue to grow in the region, pollution from urbanized areas has become an issue of primary concern. Using examples primarily from the Chesapeake Bay region, we discuss how smart growth strategies can contribute to ecosystem restoration, and provide examples of how geospatial technologies have been developed to serve as decision support tools, ending with a summary of some of the challenges that remain for sustainable urban development.