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The ancient history of Galloway has a long connection with the name MacDowall. Galloway, a district in the south west of Scotland, took its name from the Galli or Gaelic settlers of the six and seven hundreds AD. There are many legends that exist in Galloway including the story that Dovall of Galloway killed Nothatus the Tyrant in 230 BC, and it is also said that the Galloway Royal House resisted the Roman armies.

The Lords of Galloway were very powerful. Both the Scots and the English coveted the land, and the lords scattered their ancient princedom with well endowed abbeys and priories. Fergus of Galloway (1096-1161) assumed the Lordship of Galloway after he married Elizabeth, a daughter of England’s Henry I, in 1124. He was made the first feudal Lord of Galloway under David I of Scotland. The last of the MacFergus dynasty of Lords of Galloway, Alan Fitz Roland, died in 1234. His daughter Devorgilla married ‘Balliol', Lord of Barnard Castle. Their son John claimed the Lordship of Galloway through his maternal line. He was also the successful claimant of the Scottish throne in 1292.
Lands in Garthland were granted by John Balliol, Lord of Galloway to 'Dougal', a descendant of King Somerled, and Fergus MacDoual, and also a relation of Balliol. Balliol and Dougal both signed the Ragman Rolls, pledging their allegiance, along with a many other Scottish nobles, to England’s Edward I in 1296. During the reign of David II, Fergus, third of Garthland, and Dougal’s grandson, was sheriff depute for Kirkcudbright.

Clan Comyn, once the most powerful family in Scotland, were bitter rivals with Robert the Bruce over the right to the Scottish throne. The MacDowall, like their close neighbours the MacDougalls, allied themselves with the Clan Comyns. When Robert the Bruce killed John the Red Comyn, chief of Comyns, in the February of 1306, the MacDowalls became deadly enemies of the Bruces. The MacDowalls, along with the MacDougalls, fought in several battles against the Bruces. This came to an end when Sir Dougal was killed by the Bruces. Clan MacDowall changed sides many times as their priorities changed, but eventually Scotland’s defence became the most important to them and they became followers of the Bruces.
Sir Fergus MacDowall, fith Laird of Garthland, and grandson of the third Fergus, was captured at the 1402 Battle of Humbleton Hill. Sir Fergus led his Clan MacDowall men under the command of Archibald Douglas, 4th Earl of Douglas, at the battle, which was a crushing defeat for the Scots, and left the country, politically and militarily, in a precarious position. Only circumstance prevented a full scale invasion of Scotland.

Sometime near the end of the 15th century Isobel Gordon married Uchtred MacDowall the 9th of Garthland. At the Battle of Flodden Field in 1513 during the Anglo-Scottish Wars Uchtred Macdowall led the Clan MacDowall at the against the English. Both Uchtred and his son Thomas MacDowall were killed. The eleventh laird of Garthland, John MacDowall led the Clan MacDowall against the English at the 1547 Battle of Pinkie Cleugh.
In 1582 the young King James VI was kidnapped during what was called the "Ruthern Raid" to keep him protected from any Catholic influences. William Ruthven, 1st Earl of Gowrie, led the raid and Uchtred MacDowall, the 12th of Garthland was among those involved. The king was initially held at Ruthven Castle and later Edinburgh Castle.

The MacDowall name spread a lot, particularly west to Ireland during the Plantations of Ulster, and then many descendents of these MacDowalls headed even further west, to the USA during the potato famine, which hit Ireland in the mid-19th century.

The chief of Clan MacDowall as of 2011 is Prof. Fergus Macdowall. He re-matriculated the clan’s Arms with the Court of the Lord Lyon in 1987.