Circa 1900, view south east (jail indicated by red arrow)
From "History of the Town of Hillsborough 1754-1966," p. 31
"In a hundred years Orange County had at last five jails. In 1752, a contract was given to build a jail near Piney Ford. The contract was evidently not carried out. In 1755, Alexander Mebane, Josiah Dixon, and William Churton laid out the first prison in Hillsborough on Lot No. 1. Lot No. 1 was reseved for a market house, courthouse, prison, pillory and stocks.
A second jail was erected about 1765. After the second jail burned, a district jail was built in Hillsborough in 1771. Another district jail was authorized by the legislature in 1798. Building commissioners were appointed for a new prison in 1836, which was to be 45 ft. long, 24 ft. wide, and two stories high. John Berry was awarded the contract for the stone building which was completed in 1837."
The 1798 jail was burned down by a prisoner, Henry Harris, who had been captured without papers (i.e. he likely was a free person of color) some time after possibly taking part in the "Nat Turner Rebellion." He escaped, was recaptured, and was taken to Yanceyville, in nearby Caswell County, and hanged.
According to Federal and State Emergency Relief Administration (ERA) records from 1935, the "old" two-story jail and "town building" (i.e. mayor's office), which was located on the courthouse square (the jail was at the southeast corner of Margaret Lane and Court Street), was "torn down so that a proper setting could be provided for the courthouse. The demolition of the old jail was followed with much interest as it was rumored that the ancient hanging pit would be brought to light--but no trace of it was found. The walls of the old jail, which were thirty-two inches thick, made of flagstone laid in clay, provided the material for all the flagstone sidewalks built on the square."
1888 Sanborn map excerpt
1911 Sanborn map excerpt
Location of the old jail, view west, 07.31.2016 (G. Kueber)