1326 At Lindisfarne Monastry on Holy Island records show that in 1326 William de Prenderguest - being a border reiver - rendered himself notorious by plundering the brewhouse and bakehouse of that religious establishment. This was the only recorded time in 400 years of reiving that the monastry was plundered.
1333,19th July, The Battle of Halidon Hill was fought because Scotland was attempting to lift the siege of Berwick-upon-Tweed. Sir Archibald Douglas the Scottish commander attacked Englands King Edward III's army at Halidon Hill. The attack failed due to the accuracy of Englands archers and Berwick surrendered. Scotlands losses were up to 10000, while Englands were no more than a few hundred. The rout which followed the battle continued for 5 corpse strewn miles as the English knights killed at will. Probably the first rear-guard defence was organised around Ayton using the River Eye as a natural defensive barrier. The English installed Edward Balliol as a puppet king and the legitimate air (young King David) was sent to France for safety.
1336 Edward III again sent an army north in support of the puppet king Edward Balliol, who Scotland continued to resist, and laid waste as far as Lochindorb in Moray.
1338 Black Agnes Countess of the East March defied an English army for five months from the walls of Dunbar.
1346-57 King David, in response to King Philip of France plea, moved his Scottish army through the East March and descended on Northumberland pillaging as far as Hexham and Lanercost. Edward III northern barons Neville and Percy organised a defence by deploying a 15000 strong army close to Durham. Although Sir William Douglas borderers stumbled across this army and were put to flight, they managed to reorganise and Douglas commanded the right flank of the Scottish army at the Battle of Nevilles Cross. The English archers caused havoc in the Scottish ranks, whilst the English cavalry outflanked the Scots. (You would think that after Falkirk and Halidon Hill somebody would have sat down and thought about a tactic to counter English archers.) In the carnage which followed King David was captured and remained in the Tower of London for 11 years, until a ransom was agreed.
Scotland was not subdued by the defeat at Nevilles Cross and, in a minor battle at Nesbit Hill near Ayton Parish, they defeated an English army and briefly retook Berwick.
Edward III retaliated to the defeat at Nesbit Hill with vigour and his army rampaged through the Scottish East March laying waste as far as Haddington and Edinburgh.
When King David was released in 1357 he signed the Treaty of Berwick with Edward III.
1349 The Black Death, also known as the English pestilence hit the parish of Ayton for the first time, causing the population to remain virtually constant for nearly 150 years. Due to their remoteness, the Scottish rural communities were less affected than England, where a third of the population was wiped out. The black death visited the area again in both the late fourteenth and late fifteenth centuries.
1388, 19th August, Battle of Otterburn: 1402, June, Battle of Homildon Hill (now Humbleton, near Wooler): the new Earl of Douglas and Sir Alexander Hume join forces and raised an army of 10000 which looted and pillaged as far as Newcastle. As they withdrew this army encountered Hotspur Percy, who, learning from Otterburn, deployed his Welsh mercenary longbowmen with great effect. Douglas showed no leadership as his lightly armoured border spearmen fell in the arrow storm. The Scottish lines broke, following the death of about 500 spearmen, and in the rout which followed as many as 500 drowned in their escape across the river. Both Douglas and Hume were captured and held to ransom. It should be noted that once released the two shared life ups and downs and they both met their end in 1424 at the Battle of Verneuil where they were part of a Scottish mercenary army which fought with the French against an English army. This was the first serious attempt to tackle the famous English longbowmen blow for blow as the Scottish army entered the fray with a large contingent of their own longbowmen. In the battle which followed and to quote a chronicler of the time, the arrow fight was 'murderous' and 'horrible to watch' and although the English incurred large losses the Scottish army was almost annihilated. 1435 The Earl of Northumberland Englands East March Wardenat the head of 4000 riders attempted to raid the Scottish East and Middle Marches. Douglas, Warden of the Scottish Middle March, with his riders intercepted the Earls army at Piper Dene near Wark in the English East March and put them to flight. 1472 George Hume, son of Sir Alexander Hume of Dunglass, was granted the land around Ayton and so became the ancestral home of the Humes of Ayton. 1473 Sir Alexander Hume becomes Lord Hume. 1482 The Duke of Albany committed treason and conspired with Edward iv of Englands forces and Berwick changed hands for the last time. 1487 Battle of Sauchieburn, near Glasgow: King James III had attempted to curb the financial powers of the Scottish nobles. In response to losing the revenues from Coldingham Priory, Lord Alexander Hume along with other disaffected nobles conspired against their sovereign. At the Battle of Sauchieburn these disaffected nobles defeated the Kings army. The King died in the battle, with Humes East March spearmen contributing to the defeat and death of James. Immediately after the battle Alexander Hume jnr becomes the second Lord Hume. 1497 Lord Hume, at James IV behest, invaded Northern England in support of the pretensions of Perkin Warbeck. Durham and Northumberland were ravaged; in retaliation the Earl of Surrey, the renowned General of Henry VII, laid waste to the estates of the Humes and to quote the chronicler Ford 'demolished old Ayton Castle, the strongest of their forts'. Although much damage occurred, the village survived, however, Ayton ceased to be a strategic stronghold of the Hume family. In relation to this event Scott notes down in Marmion: I have not ridden in Scotland since James back'd the cause of that mock Prince Warbeck, the Flemish counterfeit Who on the gibbet paid the cheat Then did I match with Surrey's power What time we razed old Ayton Tower In September of this year, and probably to alleviate Lord Humes problems, James IV and Henry VII met at Ayton and agreed the terms of a seven year truce. This truce was probably agreed at Ayton church as by this time the castle had been destroyed. 1506 Alexander Hume III, son of the second Lord Hume becomes the third Lord Hume and also the Warden of the East March.  