The Old Tolbooth was an infamous 18th-century prison in which city?

The Old Tolbooth was an important municipal building in the city of Edinburgh, Scotland for more than 400 years. The medieval structure, which was located at the northwest corner of St. Giles' Cathedral and was attached to the west end of the Luckenbooths on the High Street in the Old Town, was first established in the 14th century by royal charter.

Over the years it served a variety of purposes such as housing the Borough Council, early meetings of the Parliament of Scotland and the Court of Session. The Tolbooth was also the burgh's main jail where, in addition to incarceration, physical punishment and torture were routinely conducted. Prisoners taken to the Old Tolbooth were tortured using implements such as the boot or pilliwinks. Jougs were attached to the exterior of the building. These were iron collars for chaining up offenders in public view, like a pillory. Spikes were also employed to exhibit body parts taken from executed prisoners.

From 1785 public executions were carried out. In 1817 the buildings, which had been rebuilt and renovated several times, were demolished.