Crail is a former royal burgh on the south coast of the East Neuk of Fife. This report focuses on the tolbooth, situated near the Marketgate. The earliest part of the tolbooth is the lower part of the tower, which has been claimed to date to about 1517. Whether this is correct, it is certain that work on the tolbooth, recorded as the ‘bigging off ane towbuth’ was ordered by the burgh council in 1598. An armorial panel survives which is inscribed with the date 160[-], which might refer to the completion of the tower. Small alterations were undertaken in the 18th century, which included the insertion of a S doorway, the lintel of which has the date 1757 carved on it. The upper windows of the tower were put in in 1776. By 1814 the tolbooth was said to be in an ‘old and ruinous state’, which resulted in extensive building work, including a large extension. Built into the S exterior wall in the west section, thought to have been part of this work, is a 12th-century scallop capital and base with moulded profile.

Crail is an ancient town, which pre-dates the Romanesque period. King David I referred to Crail as his ‘burgo meo’ in a charter of 1150-52, though the first burgh charter was only finally given by King Robert the Bruce in 1310. King David I granted pasturage in the shire of ‘Cherel’ (Crail) to the monks on the Isle of May about 1150. Ada de Warenne married Henry (d. 1152), son of King David I of Scotland, in 1139. As part of her dower, she was given the lordships of Haddington and Crail. She then gave a toft of land ‘in burgo meo de Karel’ to Dunfermline Abbey and the church of Crail, dedicated to St Macrubba, to her Cistercian foundation in Haddington (founded by 1159). It remained in the possession of the nuns of Haddington until the Reformation. Part of the present parish church structure appears to date from the later-12th century. The first mention of the church occurs in/before 1165 and a stipend was paid in 1177. In 1458, King James II of Scotland confirmed that both the parish church and the chapel of the 'beati ruffini' in the Castle of Crail had been given to the convent, this written in context of the Countess Ada and her sons. Later, in 1516/7 the parish church was made collegiate. In 1621, the priory of Haddington was erected into a temporal lordship in favour of John, master of Lauderdale, who was the son of Viscount Lauderdale. As a result, the lands of the church of Crail went to him. However, as a result of a 1587 royal grant made by James V, the church of Crail and what belonged to it had passed into the town, and in 1633 this was confirmed to the burgh.

There is no known document stating from where the two 12th-century stones built into the Tolbooth originate, but it has been noted that work on the parish church, including the removal of the medieval porch and various graves inside the church, was undertaken at a similar date to construction work on the tolbooth.

It has been said that King David I stayed in the castle at Crail, though it is possible this is a reference to the castle of Carlisle, both of which were sometime spelt with variations of ‘Karel’. The earliest definitive reference to the castle in Crail is in a charter of King Malcolm IV (1153-1165).

Although a stone carved with beakhead is mentioned in the Historical Monuments (Scotland) Commission Inventory of 1933 as being in the possession of a local resident, this stone has not been found.