A few miles from Kilmarnock, near the village of Darvel, stands Loudoun Hill. This imposing volcanic plug offers the best vantage point across the Irvine Valley and as such has always provided a strong strategic advantage. Near the bottom of the south-east slope is the remains of an Iron Age fort and nearby evidence of another fort built by the Romans during the Flavian period.

Later in the 13th century one of the earliest military successes attributed to William Wallace took place there, when a baggage train intended to resupply the garrison at Ayr was ambushed. The site most commonly associated with the battle is to the south side of the hill near the old Roman fort. Robert the Bruce fresh from his first major success over the English at Glen Trool (Galloway) in 1307, repeated Wallace’s success at Loudoun Hill when he defeated a large English force led by the famous crusader, Aymer de Vallence, second Earl of Pembroke. Bruce had had his men construct a series of ditches, forcing the mounted English soldiers towards a mire where their horses were useless allowing the Scots to defeat the larger force.

A skirmish between Government troops and Covenanter forces also took place there in 1679. Covenanters had gathered for an outlawed religious service or 'conventicle'. However, news of this meeting had reached the ears of Sir John Graham of Claverhouse who had been recently commanded by the king to suppress such events. Claverhouse mustered his dragoons and clashed with the Covenanters. This was to become known as the Battle of Drumclog and ended with Claverhouse's dragoons being soundly defeated.