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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.
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