The town that was created by an act of the Legislature in 1732 as Bridgetown (later renamed Greensboro in 1791) lay partly in Queen Anne’s County and partly in Dorchester County until 1773 when Caroline County was established. Bridgetown then was at the first point on the Choptank River that was narrow enough to cross without a ferry. The first white settlers capitalized on this fact, and the town became an important link in the portage of goods from the Chesapeake Bay to the Delaware Bay. But they were not the first to recognize the value of the area’s geographic characteristics—centuries earlier the trails of Native Americans for crossing the Choptank River had converged there.

Peter Rich, an early landowner and tavern-keeper, attracted few takers when he sought to settle his land grant at Bridgetown in 1732. His grandson, Peter Harrington, was more successful. During the boom in grain marketing after the Revolutionary War, he sold 22 lots to a variety of purchasers—shoemaker, saddler, tanner, carpenter, innkeeper, and merchants.

The town prospered, and by the beginning of the 19th century a major shipping industry had developed at Greensboro. But by 1825 it had all but disappeared, shattered by the disruption of grain exporting during the War of 1812 and the end of the Napoleonic Wars. The economy did not revive until the canning boom in the 1890s spawned 30 years of prosperity; most of the buildings in the town date from that period.

At the beginning of the 21st century, Caroline County leads the state in property value appreciation, largely due to the area’s 30-minute access to the Chesapeake Bay Bridge and Western Shore markets. Greensboro expects to share in the expansion. The Greensboro Comprehensive Plan anticipates the growth with provisions for revitalizing sidewalks, streets, and water and sewer facilities, and for preserving natural areas such as Choptank River Park. The plan emphasizes the wisdom of enhancing the visual qualities and historic features of the town.