There were many attempts by convicts to escape from the colony by water. A few were successful, many were not. In Newcastle in 1825 a first attempt to make away with a boat met with failure however an attempt later in the year proved a success....
The first was in January 1825 when seven convicts seized a government boat in the early hours of 2nd January 1825. The men William Tunnicliffe, Joseph Pritchard, Thomas Smith, James OBery, John Duncan, James Johnston and Lewis Collins were assisted by a soldier Private William Yams of the 3rd regiment.
Yams was on sentry duty at the wharf when he joined them and he brought with him his Flintlock, bayonet and ammunition. They had the audacity to take off in the Commandants gig (an oared boat). At first they had the intention of reaching the sloop Mars which was in the offing. They failed at this but got clear away and it was some time before the gig was missed and a muster held which determined that Pritchard, Smith and OBery were absent and also Tunnifcliffe who had been in charge of the light house and had taken from there the telescope.
They never really had a chance once their plan to seize the Mars failed. They were pursued by naval officer Lieutenant Thomas H. Owen in a whale boat manned by five prisoners of the Crown under the charge of assistant pilot Charles Hughes. (Charles Hughes had arrived on the Larkins in 1817, the same vessel that brought one of the absconders James Johnston). Two natives also accompanied the pursuit party.
The absconders headed south and reached as far as Reids Mistake a distance of about 15 nautical miles. Lieut. Owen reached the same place on the 3rd January where he found the oars and rudder, all that remained of the gig which had been swamped. With the help of the native trackers they soon afterwards captured five of the prisoners - Tunnicliffe, Pritchard, Smith, Johnston and Collins in a hut with Private Yams. The telescope was found with them. They were brought into Newcastle on 3rd January and lodged in the gaol.
Two other convicts who had absconded from Newcastle gaol a few days previously were also apprehended at the same time. John Duncan was discovered at the Cottage farm on the 2nd January, his clothes covered with sand and apparently much fatigued. He had been met by a constable who was in pursuit of the runaways on the road to Reids Mistake; Duncan seemed to be coming from that quarter also. OBery who was missed at the muster, returned in time for Church Services. Both he and Duncan were sent to gaol.
James Croft, Keeper at H.M. Gaol at Newcastle received into the gaol on the 2nd and 3rd January all of the prisoners. He described a second attempt that they made to escape....On the night of the 1st or morning of the 2nd February last, Tunnicliffe, Pritchard, Smith, Johnston and Collins effected their escape from the gaol by breaking through the brick wall of the upper story and lowering themselves into the yard by blankets from whence they got over the wall. They were taken a few days after and returned to their station. Duncan and OBery did not attempt to go with them.
Before Magistrate Francis Allman on 28th March, the men maintained that they knew nothing of the boat being taken in January and were merely out in the bush kangarooing. Tunnicliffe, Pritchard, Smith, Johnston, Collins were all sentenced to 100 lashes and to be transported to Port Macquarie for three years. Duncan and OBery were sentenced to 50 lashes and to be sent to Port Macquarie. 
(Lieut. Owens full account can be found in the Colonial Secretarys Papers (NRS 897) Main series of letters received, 1788-1825. 4/ 1812.p2)
Although the corporal punishment was probably administered, the second part of the punishment, transportation to Port Macquarie, didnt eventuate as the men remained at Newcastle.
The Cutter Eclipse
One of the vessels loading coal in the harbour at Newcastle in May 1825 was the cutter Eclipse. The Eclipse was built by Dillon and Bingle in 1823 and in 1825 was owned by James Haydock Reibey and John Atkinson (son and son-in-law of Mary Reibey) and used in the sealing industry in Tasmania. She was then fitted out as a packet with superior accommodation and sailed from Port Dalrymple for Sydney on 28th April. She brought a cargo of seal skins and salt as well as passengers Mrs. Thomson, Mrs. Reibey and Mr. Spencer.
After disembarking her passengers in Sydney the Eclipse continued up the coast to Newcastle where she was to load with coal. She moored in the harbour and coals were loaded from lighters by convicts. The owners paid the government an amount per ton for this service.
At nine oclock on the morning of Wednesday 11th May 1825 the ever watchful prisoners recognised an opportunity too good to resist. They seized the moment and the Eclipse was cut from her moorings.
The Australian later reported that although the men had irons on at the time, binding the master and sailors and dropping off their irons were the work of an instant.  Not only was the weather fine but the prisoners were facilitated in their escape by the sails being loosened to dry, and the master being the only one on deck at the time, so that they had only to put him below and slip the cable. There was a sentinel on-duty at the wharf when the vessel began to move, however the Eclipse was almost out of musket shot before suspicion was excited and any alarm given. The settlement was poorly equipped with vessels and the Eclipse was nearly round Nobby s Island before a boat, properly manned and armed, could be got ready.
The Australian later carried an account of the escape........ In less than two minutes the men had entire possession of the cutter. When she swung it was thought she had parted from her moorings ; but, on seeing the sails begin to be hoisted, it was immediately suspected what they were at, and alarm was given ; but before Captain Allman or Lieutenant Owen could reach the wharf she was running down the harbour with a fine fair westerly wind and ebb tide. Every effort was made to get a boat away in pursuit; but the boats crews being all convicts, did not hurry themselves to overtake her. However, they started with six or eight soldiers, under Mr. Owens orders, but their expedition was fruitless, and they soon returned. When well out to sea the pirates put the master and his crew into a boat, and sent them on shore unharmed. At twelve oclock she was just visible faraway, in the offing, steering North East and by three or four oclock the cutter was out of sight. The last time she was seen she was standing to the N. E., wind at west, and appeared to be hauling up north, under a press of canvas ; but being very crank, on account of the small quantity of coal on board, they were obliged to run her away large. We have no doubt, from all that can be learnt, that they intend for Timor. The provisions on board at the time consisted of two bags of bread, a cask of salt pork, a harness cask of beef, and a quarter of fresh beef, with about 80 gallons of water. A person who was steward with
Captain King (Jas. Johnston) in his voyage round this Island, is the navigator, and Wm. Tunnecliffe, who headed the party that ran away with Captain Allmans gig last January, is the Captain....... 
Rev. Lancelot Threlkeld who arrived in Newcastle on the Lord Liverpool on the 8th had some of his belongings sent on the Eclipse. He wrote of the incident in his journal: When safely out they ordered the captain and crew into a boat sending them on shore with their compliments to the Commandant and to say that they would not trouble him for a pilot. No other Vessel was in the harbour to pursue them of course they got safely away. It was their intention they say to take the Lord Liverpool the vessel we came down in. A few trifling articles belonging to us was in the Vessel when they went off with her. This is the third time we have lost by robbers since we have been in the colony. 
Strangely also no notice of their escape was ever printed in the Gazette. Usually brazen acts of piracy such as this were followed with weeks of notices in the Sydney Gazette. Full descriptions of the perpetrators and their misdeeds would usually be given, however on this occasion no such notice was ever published lessening the chance of their apprehension later.
Messrs Reibey and Atkinson sustained a loss of £1000 in the taking of the Eclipse. The editors of the Australian laid the blame at guards employed by the government, that due watchfulness was not exercised over these pests to society.....Surely this must have been an act of gross neglect on the part of those whose duty it was to look after the prisoners. We hope Government will not hesitate for an instant to send some vessel after the pirates; and afford every compensation to the owners.  Reibey and Atkinson had to wait eight years but were eventually compensated. (See Historical Records of Australia Vol. XVIII, pp.68, 416)
The Sydney Gazette thought that the seizure was as much owing to the laxity or carelessness on the part of the owners and crew....In the case alluded to (the Eclipse) we must say there was a great absence of common attention in those on board, or else they would not have been all below at once ! Herein consists much of the mischief. That the ships in the harbour might be cut out in some dark and boisterous night, when the wind is blowing from the South- ward or Westward, if there were no guard on board-and the same case will apply to any of the dependencies, as it should be the first thought of those on board to defend their charge from the capture of those creatures, who would be to blame were they not to avail themselves of liberty when put into their way. The Harrington, a fine and valuable brig, was cut out, in our harbour many years ago, all for want of a good look-out.
No word was ever heard again of the Eclipse or the fate of the thirteen pirates who made their escape on her. They had provisions and ammunition and a chance of finding water. They had a vessel that had been lately fitted out and the ability to sail her. With James Johnstons knowledge of the coast line, particularly the district of Port Macquarie they would have known to avoid the penal settlement and the brave and efficient commandant Captain Henry Gillman whom they knew well from Newcastle. One way or another, whether they perished somewhere far out to sea or reached the safety of distant lands they had escaped once and for all the perils of servitude..........
William Tunnicliffe was born c. 1791. Occupation seaman. He was found guilty of larceny at Chester Assizes on 5th April 1820 and sentenced to 7 years transportation. At the same time Sarah Tunnicliffe was charged with receiving stolen goods however was not prosecuted. William was admitted to the Justitia hulk on 10th May 1820 and transferred to the convict ship Elizabeth on 16th August for transportation to New South Wales. He was sentenced to Newcastle settlement for life at the criminal courts in Sydney on 25th July 1821 for forgery. In January 1825 he stole a boat and absconded from the settlement with several other prisoners - Joseph Pritchard, Thomas Smith, James OBery, John Duncan, James Johnston, Lewis Collins and soldier William Yams. He was captured and punished with 100 lashes. 34 years old at the time of escape on the Eclipse.
James OBery (Obry) (Abrey) had been assigned to Alexander Livingstone who was captain of the famous little vessel the Lord Liverpool. He was born c. 1792. Occupation Gentlemans servant. He was tried at the Wiltshire assizes on 24th July 1819 with his accomplice John Smith and sentenced to 14 years transportation for having forged bank notes. He was taken to the Laurel Hulk on 23rd September 1819 and transferred to the Coromandel on 21st October. He arrived in VDL late March 1820. In a muster taken prior to 1821 his place of birth was recorded as America. He was transported from VDL to Newcastle NSW in June 1821 having been found guilty of stealing sheep in Van Diemens Land. He was to serve out the remainder of his sentence of fourteen years at Newcastle. He was punished with 50 lashes for stealing suet belonging to
Rev. Middleton in 1822. He was punished with 50 lashes for theft in May 1823. In March 1824 he was transferred from the government gang to Alexander Livingstone. He was returned to government service before long having absconded in January 1825. He was captured and punished with 50 lashes. 33 years old at the time of the escape on the Eclipse.
Charles Day was born c. 1803. Charles Day had been employed as a waterman in England. He was tried at the Southampton Assizes on 15th July 1817 for a felony and sentenced to fourteen years transportation. He was incarcerated at Winchester and taken from there to the Laurel Hulk on 12th November 1817 where his age was recorded as 14. He was transferred to the Lady Castlereagh on 6th December in preparation for transportation to Australia. He had flaxen hair and a freckled complexion. He was disembarked from the Lady Castlereagh in Van Diemens Land in May 1818. In July 1820 he was sentenced to three years transportation to Newcastle penal settlement. In 1824 he was assigned to settler John Earle. In December 1824 he and three other men were punished with 100 lashes each on order of the bench at Wallis Plains for there being a strong suspicion that they had robbed the farm of
Dr. Moran. 22 years old at the time of escape on the Eclipse.
John Patterson (alias Wilson) had been employed by Bingle and Dillon on the wharf at Newcastle. Tides, sentries, boat crews, he had nearly three years to familiarise himself with local conditions. He was a baker by trade and was tried at the Old Bailey on 18th July 1821 and sentenced to transportation for life for stealing items of silver cutlery. He was transported on the Guildford arriving in July 1822 and was assigned to Bingle and Dillon in Sydney soon after arrival. In 1825 John Bingle and Robert Coram Dillon established a trading venture between Sydney and Newcastle. In March 1824 John Patterson was punished with 50 lashes for neglect of duty, drunkenness and absenting himself from Dillons house. In April 1825 he was punished with 25 lashes at Newcastle for insolence to his master. He would have been employed in the wharf area loading goods for Bingle and Dillon. 26 years old at the time of escape on the Eclipse.
James Johnston (Johnson) was probably the most useful of the absconders. He had once been a midshipman in the service of the East India Company and after transportation he had been selected to accompany Philip Parker King on at least some expeditions up and down the coast of NSW. On some of the expeditions Captain King landed, found water and interacted with natives. Johnston was potentially an organiser and leader. Johnston had been tried in London in December 1816 and sentenced to transportation for life. He was admitted to the Retribution hulk moored in the Thames and transferred to the Larkins on 3rd July 1817. On arrival in the colony he was assigned to John Wall at Cockle Bay and in June 1822 to John Dickson of the steam engine. In October 1823 he was found guilty of stealing from the stores of John Dickson. The crime was well organised and involved quite a number of men including Michael Crasley, William Vaughan, John Lawes, William Brown Halden and George Seager, two decent young men who had arrived in the colony free. James Johnston accompanied Philip Parker King on his expeditions as mentioned in the article above and was probably familiar with useful landing places, particularly near Port Macquarie where Kings expedition found water when they landed. 
Lewis Collins had made previous escape attempts particularly in the area between Newcastle and Port Macquarie. Collins and George Ward were tried on 11 October 1819 at Leicester Quarter Sessions for stealing articles from a coach house and sentenced to 7 years transportation. They were sent to the Justitia Hulk in November and transferred to the convict ship Neptune for transportation to New South Wales in March 1820. They arrived on the Neptune in July 1820.
Lewis Collins was sent to Newcastle in January 1821 for a colonial crime and absconded from there in April 1821. He was punished and sent to Port Macquarie where he escaped in March 1822. His description at this time was given as Native of Hawkesford west; 54 dark eyes; brown hair; and a dark sallow complexion. He was in Newcastle as a runaway from Port Macquarie in September 1824 when he was punished with 25 lashes for theft and destroying blankets in the gaol. In January 1825 he was one of the prisoners who attempted to escape in the Commandants gig.
Thomas Greenway arrived on the Dick in 1817 as a soldier of the 48th regiment. In 1822 he was doing duty as a sentry at the gaol at the limeburners near Newcastle. In the early hours of the morning of the 30th September he absconded taking with him ammunition and provisions from a store. Also absconding with him were a constable and two prisoners.. Commandant at Newcastle J.T. Morisset wrote to the authorities informing them of the break out. He described Greenway as a powerful and desperate blackguard and one of the prisoners as an old bushranger (meaning he had run before). Greenway was captured near Broken Bay and returned to Newcastle where he was punished. In March 1823 he was punished with 25 lashes for absconding from the cedar party he was assigned to. In November 1824 he was the ringleader of a mutiny that broke out in Sydney gaol and was punished with 20 days solitary confinement. He was sent to Port Macquarie where he escaped and was punished at Newcastle with 50 lashes in March 1825.
Charles North was born c. 1795. He was tried in Southampton on 2nd March 1819 and sentenced to transportation for life. He gave his native place as Andover and occupation as labourer. He arrived on the Recovery in December 1819 and was assigned to Robert Crawford in April 1822. In November 1823 he was found concealed on board the vessel John Bull with a view to escaping from the colony and sent to Port Macquarie as punishment. In March 1825 he was punished with 50 lashes for running away from the Newcastle settlement. He was 30 years old at the taking of the Eclipse.
Joseph Collins (alias Moses Solomon) arrived on the Medway in 1821, however he had been in the colony before under the name of Moses Solomon arriving on the Marquis of Wellington in 1815. He apparently left New South Wales on the Governor Macquarie bound for Port Dalrymple in 1817 (1). The Medway arrived in Van Diemens Land on 13th March 1821. By May Collins had been transferred to Newcastle, probably for a colonial crime. He was next sent to Port Macquarie where he absconded in December 1824. In March 1825 he absconded from Government service at Newcastle and was punished with 50 lashes.
William Wheatley was born c. 1791 in Gravesend. He was tried in Croydon on 13 August 1817 and sentenced to transportation for life. He arrived in the colony on the Batavia in 1818. In 1821 he was sentenced to one year at Newcastle. His occupation was given as labourer. He was transferred to Newcastle on 7 November 1821 on the Sally. In November 1823 he was sentenced by the Criminal Court in Sydney to Port Macquarie to serve out the remainder of his sentence. He absconded from Port Macquarie in January 1825 and was forwarded to Newcastle. He absconded from the gaol gang at Newcastle in May 1825. His description was recorded - age 34; 54 1/2in hazel eyes, brown hair, dark ruddy complexion. Although there is no record he would have almost certainly been punished by flogging. He was 34 years old at the taking of the Eclipse.
George Spencer was born c. 1799. He was tried in Lancaster on 21st March 1818 and sentenced to 7 years transportation. His occupation was given as cotton spinner. He arrived on the Shipley in 1818. In December 1820 he and three others were found guilty of burglary and were sentenced to 7 years at Newcastle. He was transported to Newcastle in January 1821. In 1823 the penal settlement was reduced as the Hunter Valley was opened up for settlement and many convicts were sent to Port Macquarie to serve their time. George Spencer was one of these. He was sent to Port Macquarie in September 1823 however by 1825 he had been returned to Newcastle. He was 26 years old at the taking of the Eclipse.
Daniel Delahunty was born in Tipperary c. 1802. He was tried in Tipperary in March 1817 and sentenced to transportation for life. He arrived in New South Wales on the Earl St. Vincent in 1818. He was sent to Newcastle for a colonial crime and absconded in September 1821 but gave himself up in December. In December 1824 he was one of 49 runaways from Port Macquarie. They were all sentenced to Macquarie Harbour in Van Diemens Land, however Delahunty apparently remained at Newcastle. He was the only Irish convict to escape on the Eclipse. He was 23 at the taking of the Eclipse.
George Cain (Kean) (Keene) was born in Gloucestershire c. 1805. He arrived on the Elizabeth in 1820. In February 1825 he absconded and was forwarded to Newcastle where he was to be kept at hard labour and in double irons. This extra precaution didnt stop him and he soon absconded from government service . His description was posted in the Sydney Gazette. He was captured soon afterwards and punished with 50 lashes in March 1825. He was 20 years old and the youngest of the pirates.
Notes and Links
1). Private Yams/Yems arrived with his regiment on the Hebe in 1820
 Cunningham, Peter Miller, Two Years in New South Wales: A Series of Letters, Comprising Sketches of the Actual State of Society in that Colony; of Its Peculiar Advantages to Emigrants of Its Topography, Natural History, tc
 Australia Reminiscences and Papers of L.E. Threlkeld. Missionary to the Aborigines, 1824-1859, Edited by Niel Gunson, Australian Aboriginal Studies No. 40. Ethnohistory Series No.2., Australian Institute of Aboriginal Studies 1974. p.38
 NSW Courts Magistrates, Newcastle Police Court: 28 March 1825 (Magistrate Francis Allman)