Originally a fortified Manor House dating back to the early 1200s, Hailes Castle contains some of the oldest standing stonework in Scotland. Upgraded as a fortress over several centuries the ruins comprise a 14th-century tower, a 13th century curtain wall, and the remains of ranges and towers from the 15th and 16th centuries.

It was unsuccessfully attacked twice by Henry ‘Hotspur’ Percy but later seized by the English during the Rough Wooing, when attempts were made to force the marriage of Mary, Queen of Scots and the boy prince Edward, later Edward VI. The castle’s days as a fortification were ended by Oliver Cromwell who had it slighted in 1650.