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Though a Tuckahoe Bridge
at Hillsboro is referenced as early as 1706, the community did
not really begin to develop until Elizabeth Downes laid out
building lots in 1784. The stone that forms the basis for the
town survey still stands today, as do three houses from that
original subdivision—the Elizabeth Downes house (1784-1787), the
John Corrie house (1785-1790), and the William Smith house
(1793-1800).
Throughout the 1800s and early 1900s, the town served as a
small regional commercial center. In the 1920s, there were two
grocery stores, an automobile dealership, a couple of hardware
stores, a hotel, a movie theater, a drugstore, and a soda shop.
But with the advent of the automobile and new transportation
corridors, Hillsboro evolved into a mostly residential
community. The residents are perfectly happy with its present
character, and it is unlikely that significant changes will
intrude in the near future. Over half of the town’s area is
within 1,000 feet of Tuckahoe Creek, subjecting it to the
development restrictions associated with Maryland’s Chesapeake
Bay Critical Area legislation.
Hillsboro’s residents enjoy “good-old-fashioned” community
gatherings, including an annual picnic and annual yard sale
sponsored by the town.
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