When NSW was established as a penal colony in January 1788, the settlement at Sydney Cove was envisaged as a ‘gaol without walls’.

Under General Orders issued in the 1790s, the convict population’s primary obligation was to work during the hours between dawn and dusk, with a maximum of two breaks for meals and rest. As such, convicts were only ruled by the clock, and the master or the gang they were assigned to. Outside work hours, their time was their own. Moreover, convicts could live in their own houses – it was not until the Hyde Park Barracks were completed in 1819 that some were compulsorily accommodated.

The convict populace was, to some degree, self-regulating. They were free to roam, with the first Fleet diarist David Collins noting that they ‘were everywhere straggling about’. It was hoped that the environment – and the fear of the unknown – would contain the convicts, and discourage their flight. Sydney Cove was bounded to the east by the limitless expanse of the Pacific Ocean. To the north, south and west was the impenetrable, unknowable ‘wildness’, not to mention the fear of reprisals by the local Aboriginal people.

But escape they did, either overland in search for a mythical inland sea or ‘China’, or by sea. Escapes, both doomed and successful, were a feature of life from the very first days of settlement at Sydney Cove. Within a week of landing, a party of convicts trudged south to La Perouse’s encampment at Botany Bay in the vain hope of joining the French explorer’s convoy.

The most daring – and renowned – escape from NSW was that of Mary Bryant (nee Broad) in March 1791. Mary had the good fortune to be married to Cornish-born William Bryant, who had been convicted of smuggling in 1784 and sent to Australia with her aboard the First Fleet; she had been convicted of stealing.

William Bryant was not only a seafarer, but a skilled fisherman which was a valued and well-remunerated profession in the food-starved colony. The party planned their escape months in advance, storing stockpiles of food (primarily rice and flour) as well as fishing lines, tools and nails. A compass and chart were procured from the Captain of a visiting Dutch ship, and Mary collected native Sarsaparilla to stave off sickness.

William and Mary Bryant and their two infant children, along with seven other convicts, set out on a clear moonless night on the 28th of March 1791, stealing an open rigged sailing boat and making their way towards South Head. Their escape had been perfectly timed for when there were no other boats in the harbour capable of giving chase. The escape party headed north along the east coast of NSW, around Cape York and across the north of Australia, until they ended up at Dutch Timor some nine weeks later.

Although they passed themselves off as shipwreck survivors at first, they were soon found out and imprisoned at Batavia. Mary Bryant lost her family here – William and their son Emmanuel died, followed by their daughter Charlotte. In June 1792, Mary and four of her companions were returned to England, where they were locked up at Newgate Prison. After vigorous campaigning by the writer James Boswell, the survivors were pardoned and released from gaol, with Mary Bryant returning to live in obscurity in her native Cornwall.

But the story of Mary Bryant overshadows another remarkable escape story which took place six months previously. In September 1790, John Turwood and four others travelled from Parramatta to South Head, where they stole a boat and headed north to Port Stephens. Here they lived with the local Aboriginal people for five years. The Wormi people apparently took them in – they were initiated and even took Aboriginal wives. Their ruse was up when a boat travelling along the north coast was blown off course into Port Stephens. The escape party were recaptured and returned to Sydney.

The irrepressible Turwood took to the high seas again two years later, this time with a party of others aboard the Cumberland in 1797. He was never seen again. Lieutenant John Shortland, sent on the fruitless pursuit of the boat, located the entrance to the Hunter River where he discovered plentiful supplies of coal, timber and oysters; his discovery led to the eventual settlement of Newcastle.