The area that the Kennedys are most associated with is Carrick, which at one time was the heart of the Kingdom of Carrick. Duncan, son of the King of Galloway, was granted the land in 1186 and thus became the first Earl of Carrick. Duncan’s son Neil became the second Earl of Carrick but left no male heir. The next in line was Neil’s daughter, Margaret (or Marjorie) of Carrick, later the Countess of Carrick. Upon her death 1192, the land and title were passed on to her son, Robert de Bruce, who was to become Robert I, King of Scotland.

The land itself is rolling countryside, bounded to the north by the River Doon and to the south by Galloway. Its principal rivers, besides the Doon, are the Girvan and the Stinchar, and all flow into the Firth of Clyde to the west. It is in this area that most of the Kennedy holdings and properties existed and, in some cases, still do. 

The most famous property is Culzean Castle, which is situated on a cliff above Culzean Cove. In 1777, David Kennedy hired Robert Adam to rebuild the existing castle – an undertaking that took 15 years to complete. It was given to the National Trust in 1945 by Charles Kennedy and now functions as a country day park and historical attraction that is enjoyed by thousands each year.

The second most famous is Cassillis House, which sits above the River Doon. John Kennedy acquired the lands in in the 1350s and built a strong fortification there. It has been greatly modified since then, with a square tower added in the 17th century and baronial style additions added in 1830.  It remained in the Kennedy family until it was sold in 2009.

Another property that is associated with the Kennedys is Maybole Castle, in the town of Maybole. The dark nature of its appearance is further enhanced by its history, for Lady Jean Hamilton was imprisoned there by her husband, the 6th Earl of Cassillis. She had run away with Sir Johnnie Faa, King of the Gypsies but did not get far. The Earl had Sir Johnnie and his followers hanged at the gallows tree in Maybole. Her prison was rumored to be “The Countess’ Room” at the top of the tower.

Probably the first known castle to be associated with the Kennedys was that of Dunure, which dates to the 1300s. Although it was not likely built by Kennedys, it came into their possession and was greatly enhanced in the 15th and 16th centuries. In 1563, Mary, Queen of Scots, stayed there for three days. It is also the site of the infamous roasting of the feet of the abbot of Crossraguel in 1570 to force him to turn over lands to the Cassillis branch of the Kennedys. The abbot was rescued by the Kennedys of Bargany, further adding to the enmity between the two branches. Dunure now lies in a state of ruin.

Also within these boundaries are the towns and churches that one associates with the Kennedys, including Maybole, Girvan, and Ballantrae (towns) and Kirkoswald, Crossraguel, and New and Old Dailly (churches). Robert Burns also had a connection to Carrick, as not only was his father a farmer on the Carrick border, but he himself was an excise man in Carrick. Further, he was aware of many of the tales and stories from the area. One such reference regarded that of a Culzean Kennedy who was being held in France as a prisoner of war. While he was in his cell dreaming of his homeland, his door flew open and revealed a fairy that he had befriended years earlier standing in the doorway. By freeing him, the fairy’s debt was repaid. This fairy, and others, lived beneath Culzean Castle. As Burns wrote:

“Or for Colean the rout is ta’en, 
Beneath the moon’s pale beams;
There, up the Cove, to stray and rove
Among the rocks and streams
To sport that night (Halloween).”

 Not to miss out on things Kennedy and Carrick, Sir Walter Scott wrote Auchindrane: or the Ayrshire Tragedy,which is based on the Bargany/Cassillis feud and the execution of John Muir.

The Kennedy presence in southwestern Scotland is summed up in an old rhyme:

“Twixt Wigtowne and the town of Ayr,
And laigh down be the Cruves of Cree
You shall not get a lodging there
Except ye court a Kennedy.”