The name may be derived from the Gaelic words Dun - a castle and luib - a bend. Therefore it is the fortified hill by the bend in the river. A tradition states that the De Ross first held Boarland or Dunlop Hill as their seat and a well fortified structure existed there, later the seat was moved to Corsehill.
Mr. G. Howie, of Dunlop in 1856, stated that he remembered seeing a small portion of what was said to be one of the walls about 70 or 80 years ago. It was a sort of bank, quite crumbled down and overgrown with grass. Since then, the ruins of a building of considerable extent have been removed and the ground cultivated (Name Book 1856). On the southern side of the hill there are the remains of a wide ditch or fosse, locally known as the 'Cuckoo slide' (Hutchison 1972). Paterson in 1866 states that the foundation of a ruin was removed some years ago by a late proprietor.
Pont states that the ancient strong Dunlop Castle situated by the Clerkland Burn was protected by a moat or fosse of water and had 'goodly' orchards. It was also called Hunt Hall because the Dunlops were huntsmen to the De Ross family (Paterson 1866). The whole estate was sometimes referred to as Hunt Hall.
The De Ross family were vassal to the De Morvilles, Overlords of Cunninghame. The De Morvilles backed John Balliol's claim to the crown and forfeited their lands to the Boyds, later the lands were held by the Cassillis family.
The native chiefs, although displaced from Boarland Hill were not exiled, instead they established themselves at what is now Dunlop House. The name Boarland survives in the names of Borlandhill, Over Borland, North Borland and Low Borland. The name Boarland could refer to the presence of wild boar, however a 'Boor' also meant a serf and Norman lords often apportioned lands near their castles for their servants.
The first recorded Dunlop is William de Dunlop of 1260, followed by a supporter of Edward I, Neil Fitz-Robert de Dulap of 1306. His estates were forfeited due to his support for John Balliol, as were those of the De Rosses. The family regained there lands by the mid 15th. Century and by that time we have 'of that Ilk' replacing the Norman 'de'. Sir James Dunlop of that Ilk held the estate in 1596 and married Jean, daughter of Somerville of Cambusnethan, descended from Lord Somerville. This may go some way to explaining why the Somerville family came to purchase lands at Montgomery-Crivoch and Bollingshaw in the 1800s to establish the Kennox Estate. Francis Dunlop was a witness to the disposition of the Scottish Regalia in Edinburgh Castle after the Union of the Crowns. James Dunlop of 1634-1670 married Elizabeth, daughter of Cunninghame of Corsehill and was an outstanding leader of the covenanters. John Dunlop 1748-1784 married the daughter of Sir Thomas Wallace of Craigie. She was the patron of Burns already referred to. John Dunlop Esq. MP was resident at Dunlop House in 1837 and Pigot describes it as one of Ayrshires' handsomest mansions, with the Ogrestone or Thurgatstane lying within its estate boundaries. The house was designed in 1831-34 by David Hamilton for Sir James Dunlop of Dunlop. The house is an unusual Scottish-Jacobean style, but the gate lodge is more typical of Hamilton, with strap work, classical and manorial features (Milligan). The last Baronet was Major Sir James Dunlop of 1839-1858 who died unmarried.
The last of the Dunlop to be born at Dunlop were John (1904) and Alexander (1906) Houison Crawfurd. Mrs.Houison Crawfurd is remembered for producing the first tubercular-free cattle in Ayrshire. The house was let to a number of tenants, the Henderson family of the Anchor Line being the most notable. In 1933 the house was sold to Ayrshire County Council as a home for mentally defective children.
The Clerkland Burn rivulet runs past the mansion, dividing the parishes of Stewarton and Dunlop.
In the 1600s Dunloppe had two fairs a year for the sale of dairy stock, one on the second Friday of May; and the other called Hallowday, on the 12th. of November.