Athough the actual derivation of this name is obscure, the Norman family who bore it held the Castle of Sainte Foy de Montgomery at Lisieux. One tradition asserts that the name refers to a hill and a Roman Commander called Gomericus. Roger de Mundegumbrie, whose mother was the niece of the great-grandmother of William the Conqueror, accompanied his kinsman on the invasion of England and commanded the van at Hastings in 1066. He was rewarded with Chichester, Arundel and the Earldom of Shrewsbury. He soon consolidated his possessions, and then invaded Wales, where he captured the Castle of Baldwin, to which he gave his own name of Montgomery. There was later to be not only a town, but an entire county of this name.
The first Montgomery who appears on record in Scotland is Robert, who obtained the lands of Eaglesham in Renfrewshire. He appears as a witness in a charter to the Monastery of Paisley around 1165. It is generally supposed that Robert, a grandson of Earl Roger, accompanied Walter Fitz-Alan the first High Steward of Scotland, when he came to Scotland to take possession of lands conferred upon him by David I. Eight centuries later the Montgomerys still held lands in Renfrew and Ayrshire. John de Montgomery and his brother are listed on the Ragman Roll, rendering homage to Edward I of England for their estates in 1296. A later Sir John, the seventh Baron of Eaglesham, was one of the heroes of the Battle of Otterburn in 1388, capturing Sir Henry Percy the renowned Hotspur. According a vivid Borders ballad, Hotspur and Montgomery met in hand-to-hand combat, and Montgomery carried the day. The Percys paid a great ransom for the release of Hotspur, building for Montgomery the castle of Polnoon. The hero of Otterburn cemented his good fortune by marrying the heiress of Sir Hugh Eglinton, thereby acquiring the Barony of Eglinton and Ardrossan. His son, Sir John Montgomery of Ardrossan, was one of the hostages for James I, and took for his second wife Margaret, the daughter of Maxwell of Caerlaverock. He was succeeded by his eldest son, Alexander, a member of the king’s council who was sent on several important missions to England. He was created Lord Montgomery sometime prior to 31 January 1449. Hugh, the third Lord Montgomery, supported Prince James in rebellion against his father, James Ill, and fought at the Battle of Sauchieburn in 1488. Montgomery was rewarded with the grant for life of the island of Arran and the keepership of Brodick Castle. More honours followed, and in the year after Sauchieburn he was made baillie of Bute and Cunningham. But Cunningham was claimed by the Glencairns, and a feud arose during which Eglinton Castle was burned. In either 1507 or 1508, Lord Montgomery was created Earl of Eglinton. He escaped the carnage of Flodden Field in September 1513, and was part of the Parliament at Perth in October of that year which proclaimed the infant James V king. Hugh, the second Earl, succeeded his grandfather in June 1545, but died a year later and his son, another Hugh, became the third Earl. A devout Catholic, the Earl rejected the Reformation and staunchly supported Mary, Queen of Scots, throughout her troubled reign.
He fought for her at the Battle of Langside, where he was taken prisoner. He was imprisoned and declared guilty of treason, but remained unrepentant until 1571, when he was convinced to accept James VI. He sat in the Parliament in Stirling in September of that year. Twice married, he died in 1585, leaving two sons and two daughters. His daughter, Margaret, married Robert, Earl of Winton, and their son was later to succeed as the sixth Earl of Eglinton.
Margaret’s brother, the fourth Earl, fell victim to his family’s ancient enmity with the Cunninghams of Glencairn. In 1586 the earl was riding from Eglinton to Stirling when he was attacked by John Cunningham, brother of the Earl of Glencairn, with several of his close kinsmen and retainers. Eglinton was shot dead, probably by John Cunningham of Colbeith. The Montgomerys on discovering the murder, killed every Cunningham that came in their path. Colbeith was pursued, and when captured was cut to pieces on the spot. The infant who succeeded his murdered father as fifth Earl was brought up by his maternal uncle, Robert Boyd of Badenheath. He was a favourite of James VI. When he died without issue, the Eglinton title passed to Alexander Seton as heir of line. A rigid Protestant, the new Earl of Eglinton could not accept the religious policies of Charles I, and he fought in the Army of the Covenant during the civil war. He was able to accept Charles II, who had agreed to his Scottish subjects’ terms concerning religion, and he was made a colonel of the King’s Lifeguard of Cavalry. He was captured at Dumbarton and remained imprisoned in Berwick until the Restoration in 1660.
The thirteenth Earl organised the celebrated tournament at Eglinton Castle in 1839 which set out to recapture the spectacle of medieval jousting. The present chief is the eighteenth Earl of Eglinton and ninth Earl of Winton.