In Scottish towns from the medieval period to the nineteenth century, tolbooths were the centre of local government and law enforcement.

[8][9][10] The main block and the lower portion of the tower, which would originally have been harled,[11] are made of rubble with red sandstone dressings.

[8] The upper stages of the tower, which bear a nineteenth-century clockface, are of ashlar, and are surmounted by a corbeled parapet which is drained by stone spouts.

[14]Attached to the wall of the tolbooth are two surviving sets of iron jougs, one at the north-west corner of the building about 1.5 metres (4.9 ft) above the level of the street, and one at the top of the forestair.

The whereabouts of the original medieval tolbooth are uncertain; the site and its building materials were sold by the burgh council a few years after they acquired a former church to replace it in 1570.

Of old, balls and concerts took place in the highest room of the Old Tolbooth, now occupied by the Rifle Company; and I have conversed with persons who told me that they had frequently tripped 'the light fantastic toe' there, over the heads of the miserable debtors and criminals in the prison below.

How the ladies dressed out in all their feathers and war paint, with hoops or trains made the ascent of the horrid stairs, I know not...[20]In the early nineteenth century, the tolbooth had four cells: two for debtors, and two for criminals.

Between 1815 and 1816, a new block with seventeen cells was built adjoining the new courthouse at 85 High Street, making the tolbooth redundant as a prison.

Over the course of the nineteenth and twentieth centuries the building was put to a number of different purposes, including a coastguard station, offices for a volunteer rifle company and, for a time, a glove factory.

[25] In 1805 Jean Maxwell, who was believed by her community to be a witch, was sentenced to a year's incarceration at the Kirkcudbright Tolbooth for "pretending to exercise witchcraft, sorcery, inchantment, conjuration, &c."[26] The tolbooth was used to imprison a number of Covenanters in the period after the 1660 Restoration of Charles II, when adherence to the Covenant was abandoned by the Church of Scotland and outlawed.

John Neilson of Corsock was held at the tolbooth, having been arrested for allowing ministers loyal to the Covenant to preach in his house.

In an engagement at Auchencloy several days afterwards, Graham captured a number of people including William Hunter and Robert Smith, who were taken to the tolbooth and held there until their trial and execution.

[27][31] John Paul Jones, who would go on to become a hero of the American Revolutionary War, was charged in 1770 over the death of a ship's carpenter, Mungo Maxwell.

He later died of yellow fever while serving on another ship, the Barcelona Packet, and Maxwell's father complained that the wounds from the flogging had contributed to his death.

He was freed on bail, and ultimately acquitted when testimony from the master of the Barcelona Packet indicated that Maxwell had been in good health when he joined its crew.