Hailes Castle is thought to contain some of the oldest standing stonework in Scotland. This is found in what is left of the original castle, built here in the late 1200s. The seriously ruined tower in the centre of the north range of the castle was at the heart of this: it is most easily distinguished today by its conversion in later centuries to a doocot or dovecote. Together with the rooms to its east, this formed the fortified mansion of Hugo de Gourlay and his family. There are few castles in Scotland showing masonry of 13th century date. Three are in East Lothian; Dirleton, Yester, and Hailes.

From the road, or the approach path, the castle seems to comprise just the ruins of a couple of towers and a detached stump, plus a length of curtain wall. The reality is very much more than this suggests. To truly appreciate Hailes Castle you need to see it from the far, north, side. Fortunately you can easily do so by making your way around the west end of the castle, or through the small gate in the north wall by the kitchens.

The north-west tower of the original castle contained a pit prison in its basement (exists still) and living apartments on its upper floors. At some point later in its history the interior of the building was converted into a doocot; the nesting boxes can be seen built against the lower part of the back wall. Here the castle towers over the the Scottish River Tyne (not to be confused with its better known namesake in England). From the riverbank it is still possible to gain a feel for the full scale of what was once a fine and very impressive structure. Back within the castle there remains a surprising amount to explore. The vaulted kitchens are very striking. Above them is the largest built space remaining in the castle, which the sign boards tell you was the chapel. Some sources suggest this actually served as the great hall during at least part of its life.

At Hailes the eastern half of the site was the part occupied by the original castle, and the western part by the 14th century addition. The lower part of tower "A" (see plan), the lower parts of the curtain wall extending eastward along the rocky bank of the river, and the vaulted stairway leading to a well are all that remain of the 13th century work. The tower, which was at the NW angle of the original castle, contains a dark, vaulted pit prison provided with a garderobe and air shaft; prisoners were lowered into the prison through a hatch in the roof. The upper part of the tower contained living rooms and the ruble masonry indicates a reconstruction. At a late period the interior was converted into a dovecot. The hall and other apartments appear to have been at the east end of the castle, where there are the remains of a massive outside wall, 7 feet 6 inches thick. Stone moulded details found during the operations indicate a rebuilding of this part of the castle in the early part of the 16th century.

The 14th century work is represented by the west tower "B," the lower part of the curtain wall connecting it with "A," and the massive curtain wall which now ends abruptly just beyond the entrance doorway. The tower has a vaulted basement with living rooms over. In its north wall is a pit prison, almost more horrible than the one in the older tower. The building (15th century) set between the towers has a vaulted bakehouse in the basement with a chapel over. The chapel had a doorway entered from an external wooden platform, and at the east end is a piscina and the remains of a large arched tracery window, an insertion of early 16th century date. There were buildings against the south curtain wall, and outside, extending along the length of the wall, was a great ditch which is now filled in. At the end of the 18th century the west tower was complete, and the chapel building was roofed and used as a granary.

To the south of Hailes, a mile distant, is Traprain Law or Dunpender, a fortified site of early date. During excavations on the west flank of this hill, carried out in 1919 by the Society of Antiquaries of Scotland, a remarkable hoard of silver objects was unexpectedly brought to light. The 'Treasure of Traprain', which lay buried for 1400 years, is now to be seen at the Natural Museum of Antiquities, Queen Street, Edinburgh.

The de Gourlay family supported the English during the Wars of Independence, and lost their lands after the Battle of Bannockburn in 1314. The castle and lordship of Hailes was then granted by Robert the Bruce to Sir Adam de Hepburn. The lands of South Halls and North Halls (Hailes) and Traprain, having been forfeited by "Hew de Gourlay", were confirmed by charter to Adam Hepburn from King David II. Tradition affirms that he was an Englishman who received these lands from the Earl of Dunbar and March as a reward for having rescued that nobleman from the attack of a savage horse.

Amongst other members of the Hepburn family who played a part in the history of their country were Sir Patrick Hepburn of Hailes and his son Patrick who, on the 19th August, 1388, together gallantly saved the banner of Douglas from falling into the hands of the English at Otterburn. It is also of interest to note that in 1363 Sir Patrick obtained a safe-conduct to visit the shrine of St Thomas at Canterbury, and in 1381 he was granted permission by the English King to pass through England with twelve men and twelve horses on the understanding that he was about to proceed to the Holy Land. His son, Patrick, was slain at West Nisbet, near Jedburgh, in a conflict against the Earls of Northumberland and March. Another Patrick Hepburn, who died in 1482, was created Lord Hailes, and he was succeeded by his son, Patrick, who, in 1488, was belted Earl of Bothwell for services rendered to the Crown. One member of this family was Bishop of Moray, another Bishop of Brechin, while John Hepburn, Prior of St Andrews, founded St Leonard's College in the University of St Andrews in 1512, and some years later built the fine precinct wall and towers that enclose d the Cathedral and Priory.

Owing to its situation Hailes Castle was not counted a place of Strategical importance, and played no prominent part in history. It was attacked on Candlemas 1400 by the Earl of March and Hotspur Percy, who, after burning the village of Hailes, and making two unsuccessful assaults on the fortalice, were surprised after sunset by the Master of Douglas with an armed force, and put to flight with the loss of camp and booty. The Castle was besieged and captured in 1443 by Archibald Dunbar, who "slew them that he found thairin." Building operations were in progress in 1507, as in October of that year King James IV visited the Castle and ordered drink silver to be distributed to the masons. In 1532 the Castle was burnt, and there is evidence of this on the arch of the large window of the Chapel. During the Duke of Somerset's incursion into Scotland in 1547 he passed Hailes. Lord Grey of Wilton, Governor of Berwick, when on his way to Haddington, occupied the Castle on the 26th February, 1547-48, and had the Earl of Bothwell's standard delivered to him.

The Hepburns dramatically expanded the castle during the 1300s and 1400s. The existing building became the centre of a long north range, extending to a low tower at the east end, still visible in the form of a finger of stone pointing skyward. And at the other end they built the huge four storey West Tower.  The castle was completed by a curtain wall around its south side, with a moat beyond. The end result would have been one of the best placed and most spectacular small castles in Scotland, perched on its natural rock outcrop and defended by the river to the north, the moat to the south, and thick stonework all around.

We can assume that the Castle was well furnished, as, in a letter to the Duke of Somerset, Wilton says:--"The house is fu the bigness of suche excellent bewtie within (presumably the furnishings) as I have seldom sene any in Englande except the Kinges Majesties and of verie good strengthe." In February and March, 1547-48, Hugh Douglas of Longniddry held the Castle for the English, as the Earl of Bothwell was favourable to their side. This is instanced in a minute of the Privy Council of Scotland when John, Lord Borthwick, was commanded by the Lord Governor (the Earl of Arran) to procure the Castle and "keep the samyn surlie fra our auld ynemies of Ingland and all uthairis" and not to deliver "the said place and fortalice to Patrick Erle Bothwell nor nain uthairie of his name." In July of that year French troops were encamped near the Castle.

In 1547, Patrick Hepburn, the 3rd Earl of Bothwell, opposed the Regent acting for the young Mary Queen of Scots, and was forced to surrender the castle. And a year later Hailes Castle was captured by English forces, only to be quickly recaptured by the Scots, who then removed the gates to prevent further use by the English. The end of the Hepburns' tenure came two decades later: for over two hundred years, until 1567, the Castle belonged to the Hepburns and the last of this name to own it was James, 4th Earl of Bothwell, who was the principal instigator in the plot which brought about the murder of Henry Stuart, Lord Darnley, second husband of Mary Queen of Scots.

On 27 April 1567, the 4th Earl kidnapped Queen Mary whilst en route to Edinburgh after seeing her son in Stirling. She was brought to Dunbar Castle, though they rested at Hailes enroute to Dunbar, which was also in Bothwell's hands. Depending on which version of history you believe, that he either forced her to agree to marry him, or they finalised a course of action already agreed between them, but nevertheless, on 5 May Mary Queen of Scots and James Hepburn left Dunbar for Edinburgh, where they married 10 days later. Their marriage led swiftly and directly to Mary's forced abdication, to Bothwell's flight into exile, and to the forfeiture of all of his lands including Hailes. The Castle was later granted by James VI to Hercules Stewart (a natural son of Lord John Stewart, Commendator of the Priory of Coldingham, himself a natural son of King James V), and during the greater part of the 17th century it belonged to the family of Seton.

Sir John Seton, Knight and 2nd of Baron of Barnes, acquired the lands and castle of Hailes from the heirs of Hercules Stewart sometime after his death in 1594.  Sir John Seton was an active companion of the Marquess of Montrose, and was captured with other prisoners of quality at Philliphuagh, the 13th of Sept. 1645. The castle continued as the principal residence of the Seton's of Barnes family, passing to Sir George Seton 3rd Baron of Barnes (himself likewise Knighted), heir of Sir John, who likewise resided there until 1650 and the Cromwellian Wars, during which time it was largely dismantled by Cromwell's forces. After Cromwell's victory at Dunbar, the castle was amongst the local strongholds "quitted" by the Scots: "Sir George Seton was then 4,700 in English money for troops quartered on his tenants and for damage caused by them".

Thereafter, the ruins of Hailes were abandoned as a chiefly residence by the Seton's, and it was only occupied by local tenant-farmers.  The Setons of Barnes sold the lands and ruins of Hailes in 1700 to Sir David Dalrymple, of the noted legal family, who died in 1721, and whose grandson later became Lord Hailes. While farming continued on the estate, the castle itself was used mostly as a quarry for building materials.

Eventually the Castle ruins came into the possession of the Balfour family, and the castle was given to the nation in 1926 by its then owner, the former Prime Minister, Arthur Balfour (1848 - 1930), who transferred the guardianship of the Castle to the Commissioners of HM Works, and it is now maintained by Historic Scotland.