1 October 1855

William Cannon was today found guilty of having firearms near the person of his wife, Sophia Cannon, and was sentenced to three months imprisonment in Maitland Gaol. The magistrate ordered that at the conclusion of seven days imprisonment he could be released on the following conditions, he found sureties to keep the peace for two years, 100 pound for himself and two sureties of 100 pound each. It is unlikely that Cannon would have found the 300 pounds in sureties.

2 October

1851: Today, Michael Collihane (alias- Callihane, Callahan, Micky) was executed at Maitland Gaol for assaulting and ravishing Anne Milsom against her will at Aberdeen on 10 May 1851. Upon reaching the gallows he admitted his guilt and asked for all in front of him to pray for mercy upon his soul.

1863: On this day in Maitland Gaol, a man named Henry Wilson was executed for murdering Peter Clarke at Warland's Range. It was reported that Wilson asked the hangman to adjust the rope carefully so that his death may be quick, his wish was fulfilled with reports saying a quicker death had never been witnessed.

1895: The large chimney stack was completed today inside the Gaol walls, which owing to its elevation, would prove a distinguishing mark from a considerable distance. This chimney stood 65ft (20 metres) high and formed part of a large steam cooking apparatus. The workmen who'd been engaged in the erection stated that the view from the summit was magnificent.

3 October 1936

A community concert was tonight held in Maitland Gaol. A large group of men and women gave a splendid programme of music, singing and dancing in the chapel of the Gaol. It was reported that the inmates joined in the singing of the most popular melodies. The Governor of the Gaol, Mr Mortimer, thanked the artists on behalf of the men under his control and also conveyed that the artists were doing an incredible service by giving up their time to entertain then men. He hoped that they understood how much the men looked forward to and enjoyed the concerts.   

4 October 1895

It was reported that the Department of Justice had caused a rather large inconvenience as Maitland Gaol had been connected by telegraph wires to the police stations central office in Newcastle. The people of Newcastle were concerned about how many extra wires would begin appearing around them. However the pros outweighed the cons with the department deciding that the telephone would save the Police and Gaol a considerable amount of time during the Quarter Sessions.

5 October 1945

Joseph Jones was today reported as being found dead in Maitland Gaol. Jones was a local man from Cessnock and the death was reported to the local coroner who would hold an inquest.

6 October 1880

Two prisoners arrive in Maitland Gaol today from the Newcastle Area, a young women last name Thompson and James Gibson from Plattsburg. Thompson was charged with having no lawful means of support and sentenced to six months imprisonment in Maitland Gaol. Gibson's charge is unknown.

7 October 1865

Margaret Bauer arrived to Maitland Gaol today from Sydney via Newcastle. She had pleaded guilty to the indictment of bigamy and was sentenced to six months imprisonment in Maitland Gaol.

8 October 1853

Maitland Gaol authorities were today made aware that a woman, Ann Armstrong, who was sentenced to Maitland Gaol for one month had proved to be a lunatic and they had sent her to the Asylum at Tarban Creek. The woman had come to the Gaol with her baby daughter and the Bench of Magistrates at Armidale were notified that the child still remained at Maitland Gaol under the care of another female prisoner. It was found that the baby's name was Anne Eliza Hall, but her father was unknown on her baptism record. It appears the child remained in Maitland Gaol until 1855, where she was then transferred to an Orphan School in Parramatta.

9 October 1849

As a result of a recent investigation regarding an escape from Maitland Gaol, new appointments had been made. Mr James Cox has been appointed Gaoler and Mrs Anne Cox Matron. Mr and Mrs Tristam have been dismissed. Turnkey Tierney has been promoted to the office of principle turnkey. Major Lackey has been dismissed. Constable Galvin, who was on duty in the yard when the escape took place has been dismissed and replaced by K. Rigney. In a strange turn of events it has been revealed that Mr Tristam had for some time been drawing government rations for his private servant as if he were a prisoner confined in the Gaol. The auditor general was directed to surcharge Mr Tristam for the amount drawn.

10 October

1859: Today in Maitland Gaol, a prisoner named Jane Gallagher, who had been causing problems at the Gaol was transferred. Gallagher had already been in Gaol four times within the year and was currently serving her longest sentence of 12 months, she had assaulted other female prisoners and on occasion the female turnkey. It was becoming apparent that due to the overcrowding there was little or no way of punishing her for this behaviour so she was transferred to Sydney where she continued to cause problems.

1861: Six prisoners who had been transferred to Maitland from Goulburn Gaol were transferred to Parramatta Gaol after threatening the life on a warder named John Wilson. They not only threatened the warder but also generally caused trouble throughout the Gaol having a complete disregard for prison regulations. Many of the men were guilty of serious offences including attempted rape and escape. The removal of the men to Parramatta led prison authorities to believe that Maitland Gaol would return to good order.

11 October 1895

An elderly man arrived at the gates of Maitland Gaol today after some period of time living in a destitute way. The man known locally as 'Billy Mischievous' was 84 years of age and sentenced to Maitland Gaol for six months on a charge of vagrancy. He had been in the Gaol twice in the past two years for a similar crime and always exited the Gaol clean, healthy and decent looking. Sadly Billy had been found by the Swansea Constable completely nude hiding in an abandoned cottage. He was covered in scratches and bruises and in need of warmth and nourishment. The Constable treated him very kindly, offering a warm bed at the Police Station, some of his old clothes and food. He believed that Billy's mind had begun to wander and that Gaol would be the safest place for him. It is now known what happened to this poor elderly gentleman after his release.

12 October 1940

A visit with a film projector had a lasting impression on one mission worker who recorded his feelings about the Gaol after screening a film one Sunday afternoon. He recalled it as a haunting experience when he visited one wet Sunday afternoon. Specifically he mentions the memory of the rain pelting down on some 90 men as they made their way across the flagstone yards in single file. He wrote that he felt ill as the men were referred to only by the numbers that brandished the grey prison tunics. The Governor called the next day and insisted that if he should ever return to the district that the Gaol would happily receive him as a visitor. The film shown wasn't reported upon but seemed to give great pleasure to the prisoners it was presented to.

13 October 1923

William Frewer Parsons arrived in Maitland Gaol today after being sentenced at the Newcastle Circuit Court. Acting Justice Mr Raiston sentenced Parsons to five years hard labour in Maitland Gaol, after he'd been found guilty of manslaughter.

14 October 1920

Alfred James Doonan was committed to the central criminal court on a charge of unlawfully conspiring with John Watson Brown and others to defraud the Commonwealth of 523 pounds. Doonan's solicitor pleaded leniency as Doonan had a wife and two children. Judge William Cullen sentenced Doonan to 18 months hard labour in Maitland Gaol, ensuring that he not associate with his accomplices being held in Goulburn and Bathurst Gaols.

15 October 1885

On Monday 12 October, a riot broke out in Cooranbong, as such the Police Court became very busy today. A number of men were charged with assault including, John Bourke, Richard Henry Gordon and Lawrence Kelly. John Carrick was committed to stand trial for at 4.30pm on 12 October assaulting constable John McKenzie, thereby occasioning actual bodily harm. James Walsh was also committed for causing actual bodily harm to Constables McKenzie and Jordan. A raft of men were committed for talking a prisoner named Lawrence Kelly from the lawful custody of McKenzie and Jordan. Sub Inspector Duffy was forced to make the day long trip to Cooranbong on Monday evening to sort out the prisoners and make sure they were escorted back to Maitland. He arrived home yesterday, after a rough trip with constables and prisoners in toe. All prisoners, seven in total, were lodged at Maitland Gaol this evening to await their hearing at the next circuit court.

16 October

1890: A prisoner arrived from Newcastle today to be housed in Maitland Gaol for 14 days for breach of contract. The prisoner, a coal miner, was fined 10 pound professional costs and five pound court costs for the breach, but unable to pay was forced to be imprisoned. Owing to the scarcity of coal, Bathurst who was reliant on the region for supply was forced to discontinue its street lights until the supply of coal increased.

1900: Today was the expiration date by an order made by the Supreme Court of NSW for Jimmy and Joe Governor to turn themselves into Maitland Gaol. Jimmy and Joe Governor where the last outlaws recorded in NSW. Famously known for the Breelong murders, Jimmy Governor and Jackie Underwood killed four members of the Mawbey family after a dispute over rations. Jackie Underwood was quickly caught and hanged at Dubbo Gaol. Jimmy teamed up with his brother Joe and fled the Breelong community, committing another four murders whilst on the run. The Supreme Court issued an expiration date by which they must turn themselves into the Governor of Maitland Gaol. The date came and went meaning that the Governor brothers would go down in history. Jimmy was caught on 27 October, his life would later become the basis for Thomas Keneally's 1972 novel 'The Chant of Jimmy Blacksmith'.

17 October 1855

The sum of 2,752 pounds was carried by the NSW Legislative Council for the support of Maitland Gaol. Whilst it seems like a considerable amount of money, Parramatta had almost 7,000 pounds allocated. The figure represents the ongoing struggle for regional Gaols during the mid 19th Century.

18 October

1843: Two aboriginal men named Melville and Harry are executed at the front of the Gaol wall at midday, they would be the first executions at Maitland Gaol.

1862: A letter was today sent pleading for the transfer of a prisoner named Samuel Harris, who was serving a three month sentence for absconding from service. His conduct during his time at Maitland Gaol had been most insubordinate in nature, including barricading himself inside his cell, singing and making other noises throughout the night and generally causing trouble amongst the other inmates. The staff at Maitland recommended he be removed to Parramatta Gaol where they had means to punish him for his behaviour.

19 October 1870

Tenders were today advertised locally by the Maitland Mercury and Hunter River General Advertiser for the supply of building stone. The stone would not be required until 1871, and further information about the tender could be found at Maitland Gaol.

Mr C. Stenerwald was also accepted to build additions to the court house across from Maitland Gaol.

20 October 1855

Yesterday Philip Henry McGrane was committed to Maitland Gaol on a coroners warrant. McGrane has been charged with the manslaughter of an adopted child, by giving it spirits. Today McGrane was discharged from the Gaol as the Attorney General declined to prosecute.

21 October 1922

Mr T. J. Ley, the Minister for Justice, and Mr W Urquhart, the comptroller for prisoners, had recently visited Maitland Gaol and today handed down some findings. It was decided that Maitland Gaol hadn't been built with reformation of prisoners in mind and that considerable changes needed to be made. They also wanted to see the introduction of a bonus system in the Gaol, which would permit prisoners to work in their cells during the night if their behaviour was deemed good enough. With the reopening of Parramatta imminent, Mr Ley has suggested that the long term male prisoners be transferred there. After which the changes can be made in Maitland Gaol.

22 October 1855

The seven accused from the Cooranbong riot were today taken from the Gaol to appear at the sitting circuit court in East Maitland Courthouse. With a raft of evidence presented and each accused taking the stand the lengthy trial came to a close late in the afternoon. The Jury who'd been listening throughout, deliberated for only 15 minutes before returning the verdict of not guilty for all charges against all accused persons. The prisoners were hence released.

23 October 1925

Mr P.L.K. Addison was today appointed to act as visiting surgeon for Maitland Gaol, during the absence of Dr J.J. Hollywood. Dr Hollywood would be on leave from 1 November.

24 October 1862

Today, sadly another death occurred in Maitland Gaol. A man named Benjamin Bowater in a fit of depression cut his own throat on 19 October. He was taken to hospital and was progressing favourably so was transferred to Maitland Gaol. Dr Wilton was informed and tendered to the severe wound on his throat up until his death in the early hours of the morning. His relatives were notified of Bowater’s death and the prison buried him at 9.00am the next morning.

25 October 1895

An inquiry was conducted about the treatment of seventh class prisoners, with findings reported today. The Governor of Darlinghurst Gaol thought that the seventh Class prisoner’s treatment was sufficient with young offender rates dropping from 201 to 122 in his prison. The inquiry was instigated by the surgeon of Maitland Gaol, who argues that it was not good for a boy to be confined in a solitary cell or good for his growth to have such low rations. Most of the other Gaol surgeons didn't have any objections to the treatment they currently received, however the surgeon from Parramatta suggested that the boys be given a suitable bed as the wooden plank often resulted in sleep deprivation. The Surgeon from Maitland Gaol reported that in 30% of cases he had to relax the measures to keep the boys alive. He sent a report to Dr Stuart Anderson, Chief Surgeon for the Department of Justice. Who ordered that for the next six months every youth in the program was to have their weight taken and recorded daily. Using this data he would make decisions about the conditions for the seventh class prisoners. A minimum age for this treatment would also be confirmed at this time.

26 October 1939

Tenders closed today for the removal of food waste by person registered under the Noxious Traders Act of 1902. Tenders were to be submitted to the Governor of Maitland Gaol and had to include their noxious trader’s registration number. A large notification was placed in the Maitland Mercury on 20 October making tenders aware that the lowest tender would not necessarily be accepted.

27 October 1885

A report about coal, finds in the area indicated that whilst sinking a boar for water a small seam of coal was struck underneath Maitland Gaol. The coal was found about 100ft (30 metres) from the surface. It also records a finding in the area where the East Maitland Railway Station was to be built. Due to the estimated small quantity in the finds there was no information recorded about the quality of the coal.

28 October 1865

William Paine was charged with stealing from a hut on 10 August. As the criminal sessions often ran only every three months in the state's most regional locations he was forced to wait until the next sitting in Armidale to have his sentence heard. It was alleged that he stole property of James McKenzie, who is a shepherd in the Bundarra area. It appeared that whilst McKenzie was attending his sheep Paine broke into his hut and stole a pair of blankets, several saddle straps, a pint pot, two pairs of moleskin pants, two white shirts and a cutting knife. After a short appearance and a short absence by the Jury Paine was found guilty. The Judge sentenced him to 12 months imprisonment with hard labour in Maitland Gaol. The property that was stolen was returned to Mr McKenzie.

29 October 1934

Lewis Irwin Glazier was sentenced to Maitland Gaol today after being convicted of three separate sexual offences. He was sentenced to Maitland Gaol as it was the only Gaol in NSW that had specific accommodations for this type of crime. The judge during the trail made the comment that more of this type of accommodation should be made available as the cost of transporting the prisoners from Sydney to Maitland was a burden on the tax payer. The crown prosecutor agreed, nevertheless Glazier was transferred today.

30 October 1918

Joseph Wilks arrived in Maitland Gaol today after being bought before the court on his 142nd charge. This charge was being a habitual drunkard and behaving in a riotous manner on Jack's Day. Upon sentencing Wilks to three months hard labour in Maitland Gaol, the Magistrate warned him that the next time he appeared before his court he would be sentenced to a minimum of six months in Maitland Gaol.

31 October 1916

Mr Bleasel, acting Gaoler at Young Gaol, was today appointed Chief Warder of Maitland Gaol. Sadly the Young Gaol was set to close and be handed over to the NSW Police. Despite Mr Bleasel's current position being superior in rank no position of this level was available for him. Once the NSW Police took control of the Young Gaol only prisoners serving less than a month could be detained there.