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The Convict Trail Project

John MacDonald

John Macdonald, originally from Ireland. was a boy of 17 when he was sentenced in Scotland to transportation for life for theft. He was transported on 3 September 1820 on board the Asia, arriving in Sydney on December 28th. He was assigned to Robert Crawford, at his Ellalong Property.

While he was living there, he became friendly with the Aboriginal people living around. No-one knows exactly how he came to be told or shown, but he learned from them a way to reach the Hawkesbury River from the Hunter Valley. This was known as MacDonald’s Line and ran north-east, across Mangrove Creek, through the Watagan Mountains and beside Lake Macquarie, before turning north into the Hunter Valley over Brunkerville Gap. Some influential settlers, particularly Percy Simpson, wanted this to be the route of the Great North Road, because it came past their properties, unlike the Finch Line, which took a more westerly route.

As a result of Simpson’s influence, Captain William Dumaresq, Surveyor of Roads and Bridges, arranged to have the line surveyed to see if it would be the better route. He sent Jonathan Warner out with John MacDonald to report back. Although their report said that the route was easier and shorter than the Finch line, Captain Dumaresq wrote to the Governor that he thought it would not be very useful to the rich and numerous settlers in the upper Hunter area, from Wollombi out to Broke and Patrick’s Plains. Captain Dumaresq himself was one of these people as he owned land in the Hunter Valley.

John MacDonald had an interesting life. For nine years he lived on Crawford’s farm at Ellalong, becoming a trusted labourer, until some time around 1827 when he found his famous line. After taking Jonathan Warner along this route in April 1828, he was released from his farm work for a further 3 weeks to see if he could find a line of communication (a route) from his new line to the Finch Line. It seems that he performed this task well, because in 27 September 1828, he was rewarded with a ticket of leave for his efforts. This line of communication could have been the approximate line of the road through Quorrobolong, from Mulbring to Wollombi, which runs right past his master’s property at Ellalong and would have connected it to the Great North Road, near Millfield.

He did not keep his ticket of leave for long though. He must have done something wrong and had his ticket of leave cancelled. He was sent to Newcastle penal settlement, where he injured his hand in an accident, because a report of his escape in 1833 mentions this as a distinguishing mark. In 1834, we hear of him having become a bushranger and living with the Aboriginal people up at Barraba, in the Watagan Mountains. During his time as a bushranger, he was considered to be the best bushman in the country, perhaps because he had learned so much from the Aboriginal people he had befriended. In June 1834, he led a gang in a raid on the property of Captain Dumaresq in the Hunter Valley, the very person who had supervised his work in finding roads. But his life as a bushranger did not last long. In November 1834, a newspaper reported that he had been shot in a raid on a farm at Liverpool Plains in the Upper Hunter. He would have been only 31 years old.

Reports on John MacDonald

Colonial Secretary’s Office Sydney 25 June 1828 Sir A Prisoner named Macdonald, now in the Service of Mr Crawford of Prospect, discovered a line of Road leading from Wiseman’s by Mangrove Creek to Wallis Plains which was favourably reported on by Mr Warner; — But as this line is not available to the Settlers on the upper part of Hunter’s River, Mr Crawford has been requested to allow Macdonald to be attached to the Party at Wiseman’s, with the view of discovering, if possible, a track of communication from the line abovementioned to Mr Blaxland’s Farm or other convenient Spot on the upper line.

You will be pleased, therefore, to apprise the Assistant Surveyor of this, and instruct him to report, when the Service is completed, as it is the intention of His Excellency, the Governor, to bestow then a Ticket of Leave on Macdonald.

I have the honour to be, Sir, Your most obedient servant, Alex McLeay Major Lockyer, Surveyor of Roads and Bridges


John MacDonald, Mr Robert Crawford’s Servant, who has for some time been employed in deciding the best line of Road towards Newcastle, having returned from this employment with Mr Percy Simpson’s favourable report, it is recommended MacDonald for his exertions may obtain a Ticket of Leave which was promised him if he succeeded in pointing out a good line of Road.

Wm Dumaresq

Let this man receive a Ticket of Leave as soon as Major Lockyer, who will inspect the proposed Line of Road, shall report he does not require his further services.

RD (Ralph Darling, Governor)

Published in Sydney Gazette 19th October 1828

Bushranger Report from Mr J. Warner

Lake Macquarie, August 30th 1834


I have the honor to state for the information of His Excellency the Governor that when at Kurumbung on the 29th Inst, Moses Carroll, who resides there, brought before me Kitty, a black woman whom he found could give much information relating to MacDonald and his gang (bushrangers) — she thus states that about fourteen days back she was at MacDonald’s farm and went into a small hut that he had made out of some split stuff that had been left there some time back. There were four men there besides himself, she observed four horses, sundry guns, pistols, bayonets, ammunition, numbers of knives, … Pots & each man had a watch. There was also two shirts(?) full of sugar and eight bags of flour, which they planted in the bush, except what they had in use, and they scarcely have any fire by day to provide smoak, and every night after sun down they all go to Cranky Jacks and remain there until near day light. [I asked Carroll who Cranky Jack was, he told me that he does not know his proper name but is called by the Whites, Port Macquarie Jack, he lives on a farm the property of the late Whitfield, rented to him by a Mr Coulston, this farm is at Barraba, and about two miles from Mr Bettington’s farm, which is managed by Mr Scott who was lately robbed by MacDonald.] MacDonald and his gang remain in a brush in which the hut is built, about five miles from Mr Scotts and two or three from Cranky Jacks, at the time the black woman was at MacDonalds, a strange black not belonging to the Barraba tribe came towards the hut. McDonald prevented him, got a gun and said he would shoot him if he did not go away, but the Barraba black he allows to be about him, some times the robbers take one of the horses at night and leave it the blacks camp during the times they go for plunder but two of them always remain at the hut to look after their things, she says they generally bring a load and then put it on the horses and carry it to their hut – the other four horses have ropes around their legs and feed about, one of the bushrangers asked her if she saw any white men and desired her not to tell Carroll, when she went to Kurumbung, as he would tell where they were, this woman also told me that the two men that got away from Constable Chitty (two escaped convicts had run away from him a month before while he was taking them back to Patricks Plains, where they had come from) were with MacDonald (she knows them well as she was at Carroll’s hut when Chitty called there with them on his way to my residence) she also says that she was close to Mr Scott’s when MacDonald robbed there and gave me a very clear statement of the proceedings of the bushrangers, putting all the white men into a room, as also Mrs Scott with them, who cried very much; the Barraba blacks desired her not to tell the whites where MacDonald was, knowing that she generally resides at Kurumbung.

Moses Carroll knows MacDonald well and has been acquainted with him upwards of seven years, and informs me that he is an excellent bushman and so well acquainted with the bush and passes over the mountains about Barraba, and the neighbourhood, having formerly lived with Messrs Crawford and Palmer in that vicinity, that he is very likely to remain there as long as he can supply himself with provisions and as he is so well acquainted with the Barraba blacks, they will do anything for him, as long as he feeds them, and even assist him to his attacks by an armed force. Carroll knows the place and country around about, himself and tells me if Mr Scott’s men have the least chance of sending to the bushrangers, when any stranger approaches his house, in the day or night, they would do it.

The Demise of Two Bushrangers

Sydney Times Friday 21 November 1834 Our readers will rejoice to hear of a period being put to the rapine of that notorious bushranger, MacDonald, and it is hoped of the remainder of his banditti, by the destruction of the leader and his old associate Lynch, who was conspicuous in the affair at Captain Dumaresq’s. They were both shot by a stockman of Sir John Jamison’s, in a rencontre at Liverpool Plains. — It is supposed that they are now reduced to an inconsiderable force and will soon fall into the hands of the Police.

And later: 25 November 1834 To the Editors of The Australian Gentlemen — I regret feeling myself obliged to contradict the paragraph contained in your paper of this date, relative to the statement in yesterday’s Herald of the death of the bushranger, MacDonald, which you state to be incorrect, and that he and his party are now in full force in the interior of the Bathurst Country. I have to assure you that MacDonald and Lynch were shot dead at Liverpool Plains, by two stockmen belonging to Sir John Jamison, on Tuesday the 12th instant. MacDonald was shot through the head while in the act of drawing his belt pistol, and the man who shot him was despatched immediately by His Excellency the Governor, with a mounted police force, to bring the dead bodies down the country. I saw Captain Dumaresq’s “Schalmalder” compass, which was taken from the person of MacDonald.

I am, Gentlemen,

Your obedient servant,

H C Semphill.

Robert Crawford was a wealthy property owner who had come to Australia with his brother, Thomas, as a free settler. He and his brother were granted … acres in Ellalong. He also had land at Prospect and a house in Sydney, where he worked as for the Governor. Thomas mostly ran his property at Ellalong, while Robert stayed in town.

Because of Simpson’s involvement, MacDonald’s line is now more often called “The Simpson Track”. Although it was never built as a whole road, parts of it were built. One section was built from Ten Mile Hollow down to Mangrove Creek to serve the settlers there. This old road is now preserved in Dharug National Park and is still called The Simpson Track.

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Convict Trail MapThe NEW and updated map of the Great North Road is available in visitor information centres and is also available for download here.