On 19th March 2011 and dressed in his best convict attire, COSHA Vice-President Murray Radcliffe gave us a detailed and entertaining account of attempts successful and more often unsuccessful of convicts to escape from the colonial authorities of early Sydney Town.

An Open Prison

It is a common misconception that convicts at Sydney Cove were all chained and locked up at all times. This was not so. The majority did not work in chains and were not confined after their labours had ceased for the day.

It did not take long for the newly arrived convicts at Sydney Cove to test the limits of their confinement. In the very first week after their landing, a group of convicts made the 12 kilometre trek through the bush to Botany Bay. The escapees soon found that they could not. Without the knowledge of how to find sustenance in the environment near the settlement, escapees began to starve and within a short while, either returned to the settlement, died in the bush or were killed by Aborigines.

There were two convicts who defied this rule and were successful in living outside the settlement for many years. The first was John “Black” Caesar. Black Caesar was a giant West Indian convict who came to Australia on the First Fleet. He absconded from the settlement with a stolen musket and was able to survive by stealing stores and robbing other settlers. He developed his own unique way of getting food----that is by frightening Aborigines away from food they had caught. By 1796 Black Caesar’s activities had become such a problem that Governor Hunter put a price on his head. It was five gallons of rum for the man who captured him. The reward brought a result as Caesar was shot dead soon afterwards by a settler named Wimbrow near Liberty Plains.

Another convict who was successful in living in the surrounding bush was John Wilson. Wilson was convicted in Lancashire of stealing 9 yards of cloth and arrived with 5 years still to serve on his sentence. Very soon after his arrival, he escaped into the bush, but unlike others, he was able to form a close association with Aboriginal tribes in the Hawkesbury area and could communicate with them in a form of Pidgin. He became accepted into tribal life and his chest was scarified according to tribal custom. Wilson was recaptured in 1797 with two other escapees and another seven years was added to his sentence - but he soon escaped again.

Escaping by Boat

One of the first boat escapes took place on the 1st September 1790. It was a very cheeky plan. Four convicts lead by John Turwood stole the Lightkeepers’ boat from the South Head Lighthouse station and sailed north. It is believed the group was trying to reach Tahiti.

Murray’s talk included the most famous escape story of all. That is the story of Mary Bryant. On the night of the 28th March the Bryants, their 2 children and seven other convicts scrambled into the Governor’s Cutter and quietly rowed down the harbour, out through the Heads and sailed north. Their aim was to reach the Dutch island of Timor some 5000 kilometres away. After many adventures and loss of most of her family Mary reached London and the story of her incredible adventures spread around the City. She became an object of great curiosity. While Mary was in Newgate Prison awaiting trial, the famous Diarist and Lawyer James Boswell took up her cause urging clemency and an unconditional pardon for her. In May 1793 Mary Bryant received an unconditional pardon.

Escape to Bushranging

As the colony grew in the 1820s a change took place that made it possible for runaways and bolters to survive on the land around the colony. With developments outside Sydney came roads, settlers, farms, food and the transport of valuable goods. Stealing from these places and settlers provided a means of survival for runaway convicts. Those who carried out these activities were known as Bushrangers. The survival of Bushrangers did not come from just armed robbery, but from the support from the community – either through fear, or support for their show of defiance of authority.