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The name Pitcairn, or Pitcairns, is a local one, coming from the lands of Pitcairn in the Parish of Leslie, Fife, which are claimed to be one of the oldest in the ancient Kingdom.
William de Petkaran was a juror at some point before 1249 in Dunfermline, and John de Petcarn, or Pitcairn, was given, by Sir Hugh de Abernethy, the lands of Innernethie in a 1250 charter.
Pieres de Pectarne, in 1296, pledged has allegiance to Edward I of England by signing the Ragman Roll.

At the 1513 Battle of Flodden, Andrew Pitcairn, along with seven of his sons, was killed.
In 1512 and 1518, David Petkarn, or Pitcarynn, was recorded as being archdeacon of Brechin.

It is claimed that the first shot fired during the American Revolutionary War was by Major John Pitcairn (1722-1775) of the Royal Marines in 1775 at the Battle of Lexington. Pitcairn was stationed in Boston, Massachusetts during its occupation, and it is said that he was a much respected officer by the citizens of the town.

The Commendator of Dunfermline Abbey and Secretary during the Regency of Moray, Lennox, Mar, and Morton, Robert Pitcairn was considered a great timeserver, a great enemy to Mary, Queen of Scots, and a humble servant to the Regents.

Robert Pitcairn, at the time a 15 year-old Midshipman, was the first to sight Pitcairn Island in the South Pacific in 1767. He was also, incidentally, the son of Major John Pitcairn.
The last article written by Sir Walter Scott was a notice of Robert Pitcairn's Criminal trials.
The Pitcairns prospered in Fife, and even becoming Fife Lairds, however, following their support for the Jacobite cause during the '15 and '45 uprisings, they were heavily punished.

Recorded variations of this surname include Petcairne, Petcarne, Pettcarne, Petkarn, Petkarne, Pitcarne, and Pytcarne.