Paul Musselwhite details the unsuccessful urban development that defined the region from the seventeenth century through the Civil War, showing how places like Jamestown and Annapolis--despite their small size--were the products of ambitious and cutting-edge experiments in urbanization comparable to those in the largest port cities of the Atlantic world. These experiments, though, stoked ongoing debate about commerce, taxation, and self-government. Chesapeake planters responded to this debate by reinforcing the political, economic, and cultural authority of their private plantation estates, with profound consequences for the region's laborers and the political ideology of the southern United States. As Musselwhite makes clear, the antebellum economy around this well-known waterway was built not in the absence of cities, but upon their aspirational wreckage.