Around 1780 Major Francis Boykin purchased a circa-1760 two-room dwelling with basement on a 400-acre plantation, property now occupied by the Isle of Wight County Courthouse Complex. Boykin established a tavern in the dwelling and proved instrumental in getting the county to relocate its existing courthouse from Smithfield to the property and to construct its earliest courthouse buildings there. Beginning with meetings and social gatherings held at Boykin’s Tavern, to everyday courthouse affairs during more than 200 years, the courthouse complex has evolved while serving as a center of civic and social life. The complex now encompasses four buildings: (1) The colonial and Federal-style Boykin’s Tavern, expanded between circa 1805 and 1815, with other alterations in 1902; (2) the 1801 Federal-style Courthouse, the subject of multiple building campaigns, between 1815 and 1817, and in 1903, and 1954, when it received Colonial Revival alterations, and 1987, when it was enlarged with a two-story addition; (3) an originally modest Federal-style 1820 Clerk’s Office, enlarged in 1822 and nearly doubled in 1937; and (4) a Colonial Revival-style School Administration Building, constructed in 1960 with a Flemish-bond brick exterior. The complex also boasts two memorials: A Confederate monument, erected in 1905 by the United Daughters of the Confederacy and situated in a circular green, Monument Circle; and a bronze marker attached to a granite stone that the county’s Jamestown Commission erected and placed in front of the courthouse in 1957. A brick wall constructed in 1937 to separate the original courthouse green from Monument Circle also extends the complex’s list of historic resources. From its casual beginnings within a rural setting as a county seat to its more formal, distinctive landscape by the early-20th century, the Courthouse Complex reflects Early National Period civic architecture.