Prisoners confined to the Gaol were charged with a wide range of offences such as abortion, assault, burglary, drunkenness, forgery, horse and sheep stealing, insanity, keeping a "house of ill fame" (ie. prostitution and/or gambling), murder, poisoning dogs, neglecting to maintain one’s family, seduction, and vagrancy. Many of those residing in the Gaol were there because they were destitute. In 1875, an amputee by the name of Francis Nelson Cooper was confined to the Gaol, after being charged with vagrancy. Not wanting to be a burden to the County, he wrote to Council requesting a sum of money to send him back to his native land of Ireland. Although a Committee was formed on June of that year to consider his petition, no records exist stating whether or not the sum was ever granted. He was released from the prison on July 1st, 1875 after spending 92 days as an inmate.

Others had repeat stays at the Gaol. One such inmate was Leonard Karn, who spent time at the Gaol between 1869 and 1905 for the crime of larceny. In 1877 he was charged with stealing four bags of peas and 1 bag of oats from Timothy Featherstone in West Zorra Township, though he would be found not guilty. Ten years later he was once again charged with larceny, this time for stealing buggy wheels. Unfortunately for him, this time he would be sentenced to hard labour at the Kingston Penitentiary. However, serving time at the Kingston Pen doesn’t seemed to have changed his ways as in 1891, he was once again charged with larceny and this time sentenced to Central Prison, in Toronto. In 1905, he was once again sentenced to Kingston.

In the spring of 1882, Nancy Legg was charged with murdering her infant child, George, in the Township of Dereham. After her initial conviction of performing infanticide, she was committed to the Gaol, where two years later she was declared to be insane. Over the next six years she would exhibit “good behavior” and was tasked with domestic duties, as well as granted more freedom of movement within the building. However, during this time, she conceived a child with another prisoner. As her actions were said to have disrupted the “moral tone” of the institution, it was decided she could not remain in the prison. Her adult son, living in Michigan, agreed to take both Nancy and the baby, for the sum of $5,000. In July 1890, Nancy finally left the Gaol after spending 3,122 days there. Sadly, not much is known about her, or her child, after she left the country, though it appears she passed away in 1917 in Kalamazoo, Michigan.

Along with Nancy, there were 11 other woman charged with murder in the County from 1871 to 1935. In July 1878, Mary Wilson was charged with infanticide, after her newborn child was found in the restroom of the Bank of Commerce, in Woodstock. Although there was no way of knowing for sure if the child died of natural causes or was killed, Mary was arrested and kept in the County Gaol before being found guilty and sentenced to five years at the Kingston Penitentiary. In 1913, Grace Beemer of Blenheim Township, was charged with murdering her husband, Frederick E. Beemer. Beemer died on March 25th following a three day illness. As the circumstances were deemed to be suspicious, an inquest was ordered and a grain of strychnine was found in his stomach. Although Mrs. Beemer admitted to purchasing the poison, on several occasions to kill crows, she denied having any in the house at the time of her husband’s illness. Mrs. Beemer would ultimately be found not guilty, as the sanity of her husband was questioned during her trial. Mrs. Beemer was left widowed, with 8 children, including an infant daughter who was born in the Woodstock Hospital during the term of her imprisonment.

In 1920, two returned soldiers spent time at the Gaol for crimes committed. Valentine Thomas Keough was born in St. John’s, Newfoundland, and served with the 13th Battalion during the First World War. He received a Distinguished Conduct Medal in 1918 for his heroic endeavors on the battlefield. A year later he would be charged with assault and obstructing a Police Officer at an Ingersoll Barbershop and imprisoned. He would be found guilty of all charges and sentenced to one year at Burwash Prison Farm. Samuel Bickley served in the Second Boer War and WWI, and at one time was the acting Police Chief in Woodstock. He was found guilty of housebreaking and sentenced to the Kingston Penitentiary for 2 years. In 1921 a petition for clemency was made on his behalf, though the process was delayed, as his lawyer was also defending murderer Norman Garfield at the time. It was hoped that he would be paroled at the end of  August that year, though little else is known about his case.

It wasn’t always adults that were confined to the Gaol for crimes committed. In 1856 two boys, aged 10 and 12, spent six months in the Gaol. A year later a boy of 10, classed as a labourer, entered the Gaol for a third time. In 1887 John Stewart, age 13, spent a short 5 days at the Gaol before being convicted of stealing a watch and sentenced to 3 years at the Victoria Industrial School at Mimico, Ontario. In 1890 R. Whitelaw, of Woodstock, agreed to take him on trial as an apprentice, allowing him the rate of 40 cents a day for the first year. The County approved of this arrangement, as it saved them the cost of $2/week for the boy’s maintenance at the Institution.