Lost Edinburgh: The Old Tolbooth Prison

THE OLD Tolbooth prison was an inauspicious feature of Edinburgh’s High Street for over 400 years. Today, it is considered good luck to spit on the site of its former entrance.

The Heart of Midlothian which marks where the Tolbooth Prison once stood. Picture: TSPL

The Old Tolbooth prison stood menacingly in the middle of Edinburgh’s High Street, at the north-west corner of St. Giles’ Cathedral until the early 19th century. No exact date is known for the Tolbooth’s construction, though the remnants of the building buried beneath the Royal Mile are thought to date from as early as 1386.

As the name suggests, it had originally served as a toll collection booth and was a place where merchants would set out the town’s trading rules and regulations. The bell of the Tolbooth would ring out to signal the opening of the market and also summoned councillors to the meetings of the Town Council which took place in its tower. Long before Parliament House, the Old Tolbooth also accommodated the Court of Session, a practice which came to abrupt end in 1560 when the judges threatened to relocate to St. Andrews unless better premises were provided.

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Its use as a prison, for which the Old Tolbooth would become famous, is first recorded during the 1480s. The jail facilities were further expanded in 1554 for ‘the new Prison Hous’, later imaginatively dubbed ‘Thieves’ Hole’.

Picture: submitted

The entire structure, described as being in a ‘very ruinous state’, was almost consigned to the history books in 1561 when Mary, Queen of Scots, ordered that the crumbling dual-purpose building be demolished and rebuilt. Following major repairs and remodelling, the Tolbooth persisted and by 1640 it was used primarily as Edinburgh’s main jail.

Prison life

Throughout its long history the Tolbooth boasted a fearsome reputation and was infamous for its hellish conditions and the brutal treatment of its prisoners. Judicial torture and executions were commonplace at the Old Tolbooth. Attached to the west gable, was a protruding platform equipped with a gallows to allow Edinburgh’s citizens a first rate view of public hangings. Spikes were fixed into the stone of the jail’s upper reaches to display the various body parts of those punished with the heaviest penalties. Included in this unenviable roster was James Graham, 1st Marquis of Montrose, whose head was exhibited atop the Old Tolbooth for over ten years from 1650 to 1661. In the latter years of the 17th century, prisoners would often be held at the Tolbooth before being banished to work on the American plantations.

Among the many notable inmates of the Tolbooth was Deacon Brodie, the highly-respected councillor who led an ultimately regrettable double life as a thief to fund his gambling habit. Brodie was reputedly hanged at the Old Tolbooth in 1788 using gallows which he had helped to design and finance only a year earlier.

Picture: submitted


In 1817 the ageing and dilapidated Old Tolbooth, along with the adjoining block of residential buildings known as ‘the Luckenbooths’, was demolished and replaced by the newly-built Calton Jail as the city’s main correction facility. The old jail, which had long been considered ‘an ugly encumbrance and deformity to the High Street’, caused an unwanted obstruction in the centre of one of Edinburgh’s busiest roads.

The Old Tolbooth and the picturesque tenements of the Luckenbooths had restricted traffic flow on the High Street to a passage which was only 14ft wide in places. Their demise was inevitable during an era in which conservation of historic architecture was considered far less a priority than today. However, the legacy of the Old Tolbooth has endured.


Picture: submitted

Sir Walter Scott, who managed to salvage one of the jail’s doors for his Abbottsford home, featured the Old Tolbooth extensively in his book ‘The Heart of Midlothian’ (1818) which detailed the event of 1736 known as ‘the Porteous Riots’. The title of the book referred directly to the Old Tolbooth itself and eventually led to the site of the entrance to the jail being marked out using granite setts in the shape of a heart. It has since become a local custom to spit on the heart for good luck – much to the bewilderment and disgust of the unwitting tourist.


• David McLean is the founder of the Lost Edinburgh Facebook page