This sturdy castle was raised in the 13th century, probably on the remains of an earlier fortress by the Anglo-Norman de Vaux family. Originally built of earth and timber, John de Vaux rebuilt the castle in stone. The principal building being the impressive three storey round drum keep.

In the 14th and 15th centuries the castle was considerably enlarged, to include a chapel with a pit prison underneath, hewn out of solid rock.

Built on a rocky outcrop with walls 6 feet thick and with flanking towers around its perimeter, Dirleton was believed to be impervious to the stone-throwing siege engines of the 13th century.

~ History ~

1298 ~ Dirleton is besieged by an English army led by Bishop Anthony Bek, only when a large siege engine become available is the castle finally captured.

1306 ~ Aymer de Valance is ordered to seize the castle and hand it over to the brother of John de Kyneston.

1311 ~ The castle is retaken by the Scottish army of Robert Bruce. Parts of the castle are dismantled to render it useless by the English.

1363 ~ The repaired castle is seized by William, Earl of Douglas. The castle passes to the Haliburton family.

1505 ~ Further work is in progress when King James IV visits. Patrick, 5th Lord Haliburton dies the same year, leaving three daughters, the eldest of which, Janet, marries in 1515 to William, 2nd Lord Ruthven.

1566 ~ Patrick, 3rd Lord Ruthven, and his son William, are implicated in the murder of Queen Mary's favourite Riccio.

1581 ~ William, having returned from exile in England is created Earl of Gowrie. He abducts the young James VI in the "Raid of Gowrie" and rules in his name until the King escapes.

1585 ~ Although pardoned on his exploits he is executed for his part in a plot to seize Stirling Castle. Dirleton is then granted to his great rival, the Earl of Arran, who entertains the King in the castle the same year, but eventually the estate returns to the Ruthvens. In the meantime, Dorothea, wife to the executed rebellious Earl of Gowrie, is left poverty stricken along with their 15 children.

1600 ~ John, 3rd Earl, and his brother are killed in their town house at Perth during an alleged assassination attempt against King James VI, after which the family forfeit their estate and their surname abolished. Although the maiming of the corpses of Dorothea's sons is very public, details of the entire affair remain secret. Dirleton is given by James VI to Sir Thomas Erskine, who is created Lord Dirleton and Earl of Kellie.

1625 ~ Sir Thomas's son, Alexander, sells the estate to Sir James Douglas.

1631 ~ Dirleton is bought by James Maxwell.

1646 ~ James Maxwell is created Earl of Dirleton.

1649 ~ Several men and women are accused of witchcraft and are imprisoned in the castle and later burned and strangled in the stables.

1650 ~ Cromwell sends General Monk with 1,600 men to capture Dirleton because it contains a band of Royalist horsemen known as moss-troopers who were harassing the supply lines of the main English army. The castle soon falls after a mortar destroys the drawbridge and inner gate. It is said to have been destroyed but soon afterwards was in use as a hospital for sick men of Colonel Daniel's regiment.

The ransacked castle is left in ruins by Cromwell's troops and falls into decay.