Newly discovered Peninsular War diary of Captain John Orr, a foot soldier who later helped shape military education in Scotland.
- nrwgcharity
- May 5
- 10 min read
By Rosslyn Macphail
I found, in an old family cabin trunk, Captain John Orr’s Peninsular War diary and some notes he wrote in old age. John was my great great grandfather. Also, in the trunk were papers belonging to the Scottish Naval & Military Academy, based in Edinburgh 1825-1864, which John ran as superintendent from 1831. What made him unique was how his wartime experiences enabled him to rise to prominence as a leader of military education in Scotland. Finding the diary and the various papers, sent me on a research journey which has resulted in a book about John and the Military Academy.

John was born in Greenock, Inverclyde on 3 April 1790. His father, also John Orr, was a jeweller. According to a letter which he wrote later in life, young John said he was early orphaned. After leaving school he was commissioned into the Stirling Militia but soon moved to the Edinburgh one.[1] In July 1811 that regiment was ordered to Colchester to support the British Army should there be a French invasion. Fortunately, John found that army regiments were commissioning young officers, without their having to pay for the privilege. On 3 October he was commissioned as ensign into the 1st battalion of the 42nd Regiment of Foot, the Royal Highlanders also known as the Black Watch.[2]
In a note in old age, he wrote:
I soon embarked from Portsmouth for Lisbon in 1812. Three frigates were required to convey the Regiment and we were sent to join the Army in Spain under command of the Duke of Wellington. On Lisbon, there marched to a convent and quartered there, supplied with horses and mules to carry our baggage. Lieutenant Young and I had one mule between us.
John started his diary on arrival in Lisbon on 19 April 1812. He called it ‘a journal of my actions during the campaign’. He wrote a sentence or two most nights. It is not a detailed diary, but it has an immediacy, which makes it valuable. He was an excited 22-year-old who had never been abroad before and was enjoying this adventure and was curious about his surroundings. An early diary entry:
Lisbon is a very fine town but rather irregular and the streets dirty as they take no trouble in cleaning them although it would be very easily done. The town, with the exception of a small part stands on the face of a hill on the side of the Tagus. The country all around is most beautiful and in a high state of cultivation. I went to see the church of Sao Roque and was shown some elegant silverwork and some beautiful mosaic paintings in the church. I also went to the opera and saw some fine dancing.

On the 8 May they left Lisbon to march to Ciudad Rodrigo, across the border in Spain to join the Allied Army. When they reached Nisa, it was decided that the regiment should be reorganised. Young officers from John’s battalion were to be sent back to Scotland with the 2nd battalion. John did not want to go home. He described the situation in a note written in old age:
…. as I did not wish to return, I applied to Colonel Stirling to use his influence to keep me out and told him I wished to see some fun and if I go home I’ll soon be ordered out again. On my asking him he said ‘Well Sir you put that in monochrome’ and I did so.[3] An order came at once for me to remain out. My request was granted and the following day, the Old Col said to me on the line of march ‘Well Orr I’m glad to see you have some spunk in you.
On 17 June they neared Salamanca where the French had left a garrison of 800 men in a fortified convent which was being besieged by Allied troops. Two days later John wrote:
‘The army was drawn up in battle order on the heights of the north side of the Tormes as the enemy was endeavouring to relieve the garrison. It was there that I first heard the roar of war and shot flying over me.’
The evening before the Battle of Salamanca, they crossed the river Tormes. Here is John’s short report of the battle which took place on 22 July 1812:
Halted about 12 at night in a ploughed field. It there began to rain accompanied with thunder and lightening which seem to threaten both armies. Next morning the whole allied forces were put in motion and after some manoeuvres about 4 o’clock both armies came to close engagement and about 6, victory favoured the British, at 7 the French were in full retreat. They lost 20,000 in killed, wounded and prisoners. Marmont was wounded. [4] [5] In short the French seldom or ever got such a drubbing.
After the battle most of the British forces went to Madrid, but rather than stay there, Wellington decided to follow the French north. They arrived at Burgos on 18 September 1812 and were confronted by a large medieval castle on a high plateau separated by a narrow valley from another part of the hill, which had a smaller fort on it. Wellington ordered a siege and a number of siege trenches to be dug in spite of the fact that he did not have a siege train with him. John wrote on the 19 September.:
Our Regiment was ordered to support General Pack’s Brigade in storming the out fort of the castle at Burgos, but after getting to the top of the hill they thought it better that we should both storm and support……The attack began after dark and lasted about 20 minutes. Our regiment entered in a style becoming the Royal Highlanders. We had two Lieutenants killed and a Captain and Lieutenant wounded.[6]
John was wounded in this assault, although he does not describe it in his diary. From 20 September onwards there are no entries for a week. John then wrote on 28 September:
I have been in the hospital today at Villa Torro and the sight is melancholy indeed, to see fine stout young men laying some wanting legs others arms.
Presumably John was visiting the hospital because of his wound. He perhaps did not write about it in his diary as knew other men were much more seriously injured. A surgeon who attended him later wrote that he had received ‘a severe contusion in his left arm from the splinter of a shell’.

The surgeon went on to say that he wanted to report John’s injury as he considered he was unfit for duty, but John had persuaded him not to do that. Years later John wrote ‘I did not wish to alarm my friends at home. Also had always a strong aversion to get to the rear [underlined in letter] when I was in any way able to do my duty with the Corps’.
Despite his injury John continued to serve in the siege trenches where there were many deaths and injuries.
On 4 October:
Was in the trenches all night as a covering party and was pretty hot work of it. But thank God I got safe off, although the only remaining officer …. for both the Captain and the Lieutenant were wounded. I lost about 10 or 12 men and some 20 to 30 wounded.
The siege continued and the weather worsened, being both cold and extremely wet. Eventually Wellington heard that the French were approaching to relieve the siege and on 21st he gave the order to retreat. He later admitted it was ‘the worst scrape that I was ever in.’
This is John’s entry about the order to retreat:
I thank God when we were ordered to the front from the trenches at about 1 o’clock. Got orders to send the baggage to the rear at 2 o’clock and at 8 at night began to retreat. We marched through Burgos and passed under the fire of the castle but the enemy did not see us.
At Salamanca Wellington hoped to make a stand but the strength of the advancing French troops meant they had to retreat a further 90 miles southwest, which took 4 days. It was still very wet. John wrote: ‘We had a most fatiguing retreat all the way to Ciudad Rodrigo for the enemy kept close up in our rear’.
He added:
I was on the baggage guard the same day Sir E Paget [Sir Edward Paget] was taken prisoner and I near sharing the same fate.[7] I marched all night and next day got into Rodrigo many a dead animal and body lay on the road. After passing Rodrigo we got into houses at night which we stood much in need of as the weather was very wet.
There was no fighting during the winter and the 42nd were based in Portugal in Seia. John wrote little during this period as ‘what happened since we got into winter quarters is no consequence’. He did, however, note an unusual event which made an impression. He was out walking one evening with his friend Lieutenant Young and he wrote:
I saw an old woman in the act of digging a grave at the side of an old wall, beside her lay the body of a dead child. It is custom in this country that when an unfortunate girl is with child she is brought to bed secretly and the infant is put in a sort of wheel [this is a turntable called a foundling wheel built into the wall of probably a convent] which runs round and the people in the inside take the infant which is supported at the public expense by the juiz de fora.[8] [9] This often prevents murder.
John became ill with a fever while in Seia but was fit when the campaign restarted at the end of April 1813. They set out to march north towards the Cantabrian Mountains to drive the French out of Spain. They managed to cover a distance of about 350 miles in under a month – a remarkable achievement.[10] On the 6 June John was delighted to hear he had been promoted to Lieutenant. They continue moving north and passed through the town of Laguardia where they were ‘viva’d’ by the people.
The next weeks were spent in the mountains moving from village to village and having skirmishes with the French. On 1 August they reached the Pass of Roncesvalles, near the French border. John reported that they often saw wooden houses deserted by the Spanish where the people had fled to the hills. John was shocked as ‘the French did not leave a house without plundering everything within.’
In November he heard that his uncle had died and he asked for leave to return to Scotland, which was granted. He then served with the 42nd Regiment in Ireland until in May 1815 when the battalion was ordered to Brussels for a confrontation with the French Army under Napoleon.
John fought with the 42nd at the Battle of Quatre Bras on 16 June 1815. In later life he wrote a note about an encounter during this battle:
At Quatre Bras I commanded a company and did duty as Adjutant …The enemy had a gun on our flank we were formed into a square. A man was tardy and slow in turning and I took hold of him by the arm and said “Come up Sir” I felt the wind of a ball whiz through the air and it struck the man, knocked his head off, the brains spattered about, some on my coat. The French cavalry were only a few yards off and I gave a yell and shouted ‘Charge’ and we did so and drove them off.
This incident occurred when the 42nd was ordered to move forward through a field of rye as high as their bonnets. The companies were then charged by a group of French Lancers. Initially the Royal Highlanders thought these mounted troops belonged to the Duke of Orange and halted to let them pass. When they realised their mistake, their commanding officer Lieutenant -Colonel Sir Robert Macara, tried to form them into a square, which eventually had several wounded Lancers within in it.[11]
The 42nd suffered a huge number of deaths and injuries at Quatre Bras. As a result, Wellington kept them in reserve at the Battle of Waterloo which was fought two days later.
The 42nd did not enter the action until about 2pm, when they were ordered to charge. John received a musket ball wound to his left leg and was carried from the field. After the battle all regiments went to Paris. In the archive there is a copy of a letter from the field hospital in Paris where John was taken, describing his injury as ‘a severe contusion to the left knee by a musket ball.’[12]
He was fit to return to the UK with the 42nd in December 1815. The regiment eventually arrived in Glasgow in September the following year. A few months later the 42 nd Regiment was contracted and John was put on the half pension list. During the next four years, he managed to join two other regiments, but each in turn was disbanded. The size of the British army was greatly reduced after the victory at Waterloo. In 1821, John aged 31, was retired again but this time on full pension.
In 1831 he was recommissioned into the Edinburgh Militia as a captain.[13] Shortly after this he was appointed superintendent of the fledgling Scottish Naval & Military Academy which had had a slump in its enrolments due to mismanagement. John’s military experiences gave him the knowledge, resilience and discipline, to turn the only Military Academy in Scotland into a successful college. Under his management, the Duke of Wellington became one of its Presidents. It became an internationally known institution, sending over 1000 men into the various services. He retired, aged 74, in 1864.
Many years later, friends found out he was in financial difficulty. As a tribute to his military service and his years as superintendent, John, now in his 90th year, was presented with a purse of 300 guineas (£30,000) and a pair of silver-plated vases.[14] The money was raised by 96 past pupils and various friends.[15] A few weeks after this John died on 6 December 1879 and was buried in Warriston Cemetery in Edinburgh. He was the last of the Black Watch officers who had fought at Waterloo.
There is more about John’s life and the history of the Scottish Naval & Military Academy in my book Fighting Napoleon to the Scottish Military Academy: The Life of Captain John Orr. Published by Pen & Sword on 11 October 2024.

[1] Both commissions in family archive.
[2] Commission in family archive.
[3] To apply officially in writing.
[4] It is thought now that John’s figure of 20,000 is too high.
[5] French General: Marshal Auguste Marmont
[6] Papers in the family archive report that John received a wound to his arm during this assault.
[7] General Sir Edward Paget (1775-1849). He was a prisoner for two years and was freed at the end of the War.
[8] This is a foundling wheel. It is a type of turntable in a wall of a convent or similar building. Babies born illegitimately were put on the wheel and it was pushed round, so that the baby could be taken care of by the nuns inside the convent. The foundling wheel, or ruota, was introduced in Italy in the year 1198 by Pope Innocent as he was distressed with the number of infants who were found drowned in the Tiber river.
[9] Juiz de fora was an independent judge.
[10] Charles Esdaile. The Peninsular War, (London: Penguin Books, 2003), p 444.
[11] Victoria Schofield, The Highland Furies. The Black Watch 1739-1899 (Great Britain. Quercus, 2012), p 352.
[12] Certified copy of the letter from St Denis hospital. Family archive.
[13] Commission in family archive.
[14] Glasgow Evening Post 15 October 1879
[15] List of contributors in the family archive.
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