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The Battle of Philiphaugh


Following their victory at the Battle of Kilsyth in August 1645 Montrose and the Royalists found themselves in a very strong position indeed. All the Covenanting forces which had been sent against them in the previous 12 months had been defeated, with considerable loss, and all those Lords and nobles who had heretofore been hostile to the Royalist cause now flocked to Montrose to proclaim their allegiance. He was now effectively the master of Scotland.

The Burgers of Glasgow had themselves come to Montrose when he was on his way to that city and offered a sum of £500 in order that Montrose might keep his army outside the city walls. This money was accepted initially but soon returned by Montrose as a gesture of goodwill. This was one of the many gestures which were to ultimately prove his ruin.

Some of the Royalist army did come into Glasgow under promise of good behaviour and there was an occasion when Montrose had to order the hanging of one or two soldiers who couldn’t resist the temptation to loot. The fact was however that Montrose’s army was unpaid and they looked upon it as a right to help themselves to the spoils of war. Following Kilsyth the victors had been looking forward to the sack of Glasgow but Montrose’s position had changed in that he now represented law and order in the land and he had to be seen to be offering protection to all; even those who had previously been hostile to him. The highlanders and Irish had been denied the sack of Glasgow, and they were unhappy about it. As a result of this act of clemency many of the highlanders drifted away.

At the same time Montrose sent Nathaniel Gordon and The Master of Napier east to Linlithgow and Edinburgh to ensure the release of the Royalists imprisoned there. From these prisons were released Wishart, Lord Ogilvy, Stirling of Keir and his sisters, The Earl of Crawford and many others who had been either captured like Wishart or simply thrown into jail by Argyll for their allegiance to Montrose. All together over 130 prisoners were released, all supporters of Montrose and the King.

Montrose next moved his leaguer to Bothwell and it was to here that Sir Robert Spottiswoode came directly from the King with papers appointing Montrose Captain General of the King’s forces and Lieutenant Governor of Scotland in the King’s stead. Effectively Montrose now ruled Scotland in the name of Charles 1st.

One of Montrose’s first acts was to appoint a Session of Parliament to sit at Glasgow on the 10th October 1645. He then knighted his Major General Alastair MacDonald and held a day of celebration upon which many of those who had previously withheld their support for Montrose came forward to offer their allegiance. Many of those who now came forward were doing so out of political expediency and their allegiance would change in accordance with whichever way the wind blew. Montrose was desperate to bring everyone together under the King’s banner however and all were welcomed and given pardon on trust. It is a trust which many were to forsake.

It is ironic that Montrose, now at the zenith of his power, should display such weakness to his enemies. But he was now acting as the King’s representative and he had to exchange the sword for the hand of clemency.

The Army Fragments

Towards the end of August 1645 Montrose’s fortunes began to suffer. Firstly, Alastair decided that he wanted to renew his personal campaign in the west and he left the Royalist camp taking with him all the Irish except those who remained loyal under Magnus O’Cahan. Alastair had a legitimate reason for leaving but he did it in the most careless way possible, leaving Montrose severely weakened in infantry.

Following this Lord Aboyne defected claiming a summons from his father. He left taking all the Gordon horse other than those few who remained with Nathanial Gordon and the Earl of Airlie. This left Montrose with an army of 700 foot and around 200 horse. The Earl of Douglas did come in with around 1200 infantry but they were raw levies and could scarcely be expected to fill the shoes of the veteran Irish and Gordon’s who had left with Alastair and Aboyne.

The reasons for these defections are not difficult to identify. After Kilsyth the highlanders and Irish had been expecting, but were denied, the sack of Glasgow. Many of them became disaffected when what many of them considered their just reward was not forthcoming. Lord Aboyne was incensed when he was replaced as commander of Cavalry by the Earl of Crawford, recently released from gaol. Thus two of the Royalist mainstays in the recent campaigns, Alastair MacDonald and Aboyne, rightly or wrongly felt aggrieved and responded by leaving the Royalist army. The result of this was to prove disastrous for Montrose and the Royalist cause.

This period in the campaign marked a watershed for Montrose in the tactics which he tried to employ in the Royalist cause. Up until now all the victories which the Royalists had enjoyed had been won on the strength of the Highlanders and Irish. Montrose however had never tried to hide the fact that his ultimate aim was to lead a proud and victorious loyal ‘Scottish’ army south over the border to support the Royalist cause in England. Whilst Montrose’s intentions were without question honourable he was perhaps rather naïve in this wish and many of the problems which he faced were similar in many ways to those which would be faced 100 years later by Charles Edward Stuart.

The highlander was without doubt a ferocious adversary when at home in the glens and straths. Discipline was never one of the highlander’s strong points however and highland armies were accustomed to melting away after a victorious conflict to carry off their booty or perhaps to attend to harvests. The highlander always fought better in his own backyard.

Yes, the highland host did reach as far as Preston in 1745 when Bonny Prince Charlie made his attempt on the throne but the further south the army pressed into England the more unsettled it became and retreat became inevitable.

Thus in September 1645 Montrose found himself in borders country, hostile territory, with only a few hundred of his loyal veterans. Why then, when most of his army had left him, did he not make the decision to about turn and seek the safety of the highland fastnesses to regroup and regain his strength?

The March Southwards

Although traditionally of Covenanting sympathy, the border Lords Home, Roxburgh, Traquair and Douglas had come to Montrose after Kilsyth to make their peace and declare their loyalty to the King. Montrose saw this as his chance to take the campaign south and he gambled on the potential loyalty of these border Lords against the proven loyalty of those who had carried the campaign to date so effectively. The Earl of Douglas alone honoured his promise to Montrose but the 1200 men whom he gathered were untrained and inexperienced. Traquair sent his son Lord Linton to Montrose with a troop of horse but there is strong evidence to show that his only contribution was to betray the Royalists before the battle of Philiphaugh.

Home and Roxburgh, having declared their loyalty to Montrose, hurried away supposedly to recruit. In reality however they allowed themselves to be captured by the Covenanters, thus saving face. They lost no time in updating the Covenanters on the position and the weakness of the Royalist force.

Leslie Advances

The situation in Scotland during 1645 had been watched closely by General David Leslie who had been leading the Scots army fighting in England on the side of the Parliament. Leslie was concerned at the reported Royalist victories during 1645 and when the Covenanting defeat at Kilsyth was reported to him he decided that he could no longer remain in England.

So it was that, as Montrose was leading his weakened force south in the hope of crossing the border, Leslie led a force of 5000 mounted troopers north in the hope of being able to extinguish the Royalist campaign.

Leslie was not fully aware of the precarious state of the Royalists nor was he aware of their exact position, so in a swift advance by the east coast road he crossed the border and had gone as far as Gladsmuir, 15 miles east of Edinburgh, before he learned that he had in fact passed the Royalists by a considerable margin. Now though he was behind the Royalists and could easily bar their line of retreat to the north.

Montrose had heard rumours of Leslie’s advance but he continued his march south, reaching the field of Philiphaugh close to Selkirk, on 12 September. He ordered his troops to camp here still hopeful that reinforcements from the borders lords were on their way to join him. The field of Philiphaugh is a flat river haugh which lies to the west of Selkirk, at the junction between the Ettrick and Yarrow waters. The Royalists camped on the northern bank of the Ettrick water, just below its junction with the Yarrow. The position benefited from the protection of the water and the Irish erected breastworks to protect their right flank.

Leslie was now beginning to learn of Montrose’s weakness in numbers and he also learned, most probably from Traquair, where the Royalists were situated. He quickly realised that he had been presented with an incredible opportunity to catch the Royalists out and he turned his force south and set off in pursuit.

The Royalists meantime had camped down for the night. The Royalist cavalry was billeted in nearby Selkirk and Montrose himself lodged in a house, the site of which is marked today, in the West Port. Montrose left the positioning of lookouts to his captains and then retired to his lodgings to start writing his reports.

The events of the night before the battle are unclear but, with Leslie advancing during the night, it appears that one of the Royalist outposts, troopers of Charteris of Amisfield, were surprised and routed with loss near to the hamlet of Sunderland, barely 4 miles from the Royalist camp.. Although this news was received back in the camp it was misinterpreted as simply a drunken brawl and the decision was taken not to escalate the information to Montrose.

Lord Linton with his troop of horse withdrew without warning during the night, giving credence to the theory that he had been warned, perhaps by his father, about the events which were to unfold early the next morning.

General Leslie had advanced on the Royalists during the night and near to Philiphaugh he split his force into two. His own force advanced down the left bank of the Ettrick and the other, under the command of Middleton, approached the Selkirk Road by way of Will’s Nick, closing the trap shut. As dawn broke on the morning of 13 September 1645 the river haugh was shrouded in a thick cloak of mist. Leslie’s forces had benefited from this as they took their positions and prepared to unleash their assault.

Map reproduced with kind permission of HM Ordnance Survey

The Royalists were just beginning to stir from their slumber when Leslie’s troopers thundered across the river haugh. Their night advance had not been in vain; the Royalists had been caught entirely unawares. As more and more troopers advanced on to the haugh the Royalists quickly tied to mount some defence of their position. Without striking a blow however the Douglas levies quickly broke and fled, leaving the 700 or so loyal Irish veterans and highlanders to fend for themselves.

Montrose first became aware of the conflict when his chief scout Captain Blackadder stumbled into his lodging shouting that the Covenanters were upon them. Montrose grabbed his sword and jumped on the first horse he could find and galloped down the brae towards Philiphaugh. When he arrived there he found Magnus O’Cahan’s Irish bravely manning the breastworks and holding back almost ten times their number of mounted troopers. Montrose gathered as many cavalry as he could, around 50, and led a series of frantic charges upon the Covenant horse, desperate to try to relieve the defenders of the breastworks. For a short time this plan worked and momentarily the Covenant advance was checked. The Royalist horse could not sustain this effort for long however and soon their casualties began to rise. The sheer weight of the Covenanting horse then began to tell and Montrose’s small band could do no more.

Montrose was distraught at the plight of the Irish and he resolved to mount one last suicidal charge on their assailants. The small group remaining with him however advocated withdrawal arguing that as long as Montrose remained alive the Royalist cause in Scotland would also. Realising that what they said was true Montrose gave way and the small party led him from the field. As they fled the Irish were standing resolute but with mounting casualties. It was only a matter of time until they would be overwhelmed. Montrose knew that he was leaving the flower of his army on the field; the loyal Irish who in the last 12 months had swept aside every force the Covenant could put in the field against them. He knew he was leaving them to their fate and it was something which would haunt him for the rest of his life.

Defeat and Surrender

Montrose’s small band fled North West over the Minch Moor. They were being hotly pursued by a troop of Covenanters when they about turned and attacked them, remarkably, capturing two colours in the process. Continuing on their way the Royalists arrived at Traquair House seeking help. The Earl of Traquair was not home to the defeated however and the doors of Traquair House remained closed. The Royalists continued on westwards not stopping until they came to Peebles, where they rested awhile.

Back at Philiphaugh, realising how desperate their situation was, the Irish agreed to surrender under terms agreed with their senior surviving officer Adjutant Stewart. The Irish were promised quarter upon surrender of their arms. With their disarming achieved however the Clergy of the Covenant claimed that the Irish were unworthy of such generous terms and they demanded that the thousands of Covenant slain in the previous conflicts should be avenged. General Leslie was initially against such action but eventually, on the premise that the surrender terms were only meant for Adjutant Stewart and not the Irish, he gave way to the pressure from the Clergy.

In as dastardly an act as could be imagined the unarmed Irish were marched to the courtyard of nearby Newark Castle and there they were slaughtered to a man. The bodies were buried in a mass grave in nearby Slain Man’s Lea. Of all the atrocities which were perpetrated by both sides during the civil war, and indeed the brutal Thirty Years war fought on the continent, surely none could be as base as the slaughter which took place, after an act of surrender, upon the Irish at Philiphaugh. To compound this act, following their victory the Covenant troopers fell upon a group of 300 helpless camp followers near the battlefield, many of them Irish women and children, and slaughtered them with unimaginable cruelty. Such was the justice of the Covenant.

Newark Castle – Scene of the slaughter of around 300 Irish troops who had surrendered to the Covenanters on promise of quarter.

The Aftermath

Montrose continued on his flight north and within 2 days was back in the security of Atholl. Remarkably he had managed to gather around five hundred fugitives from Philiphaugh and, notwithstanding the major losses he had suffered there, he set about regaining his strength and continuing the Royalist campaign in Scotland.

Although the Philiphaugh incident was a major blow to the Royalists the fact was that the great majority of the Royalist army which had won the resounding victory at Kilsyth two months before was still intact. MacDonald was in the west with his Irish veterans and the Gordon horse was in the north. The loyal men of Atholl too were spared the catastrophe at Philiphaugh and surely they would rise again.

The fact of the matter was however that the spell had been broken; the stunning series of Royalist victories won in the last 12 months had been ended; Montrose had lost his invincibility and the Royalists had lost their momentum.

During the next few months Montrose did continue campaigning in the north but all that came to an end when Charles 1st surrendered to the Scots army at Newark in April 1646 and, as a result of that surrender, Montrose was ordered to disband his forces. This he did reluctantly at Rattray near Blairgowrie in July 1646. Such was the loyalty of his army that many of them pleaded with him to continue the struggle alone, or to take them with him on his banishment to the continent. Naturally, he was unable to do either. Some weeks later, having avoided a Covenant trap to capture him, he managed to take ship from Scotland to the continent.

Montrose would return to Scotland some 4 years later but the magic was gone and his disastrous defeat at Carbisdale in April 1650, compounded by some double dealing by Charles 2nd and the Covenanters, sealed his fate and would soon after lead to his barbaric execution in Edinburgh at the hands of the Covenanters.

The site in the West Port where Montrose spent the night before the battle.

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