Cambridge

The seat of Dorchester County and, with around 13,100 residents, the fourth largest town in the Eastern Shore region. Founded in 1684, it is among the oldest settlements in Maryland, and its port on the Choptank River made it a trading centre for the surrounding tobacco plantations, including a slave market. The town later boomed on food processing: the Phillips Packing Company held the contract to supply American troops in both world wars and employed more than 10,000 people at its peak. The collapse of those jobs in the 1960s, combined with severe racial unrest that brought in the National Guard, left decades of decline that the town is still working through.

The waterfront and the historic High Street corridor are the parts worth seeing, with brick townhouses, the county courthouse and views over the Choptank. Rapper Jay-Z lived here briefly before his breakthrough.