‘Convict uprising at Castle Hill, 1804’ (National Library of Australia, nla.pic-an5577479, watercolour).
One of the earliest and most significant outbreaks of internal unrest in Sydney occurred near Parramatta in 1804. This was the convict uprising which centred around Irish convicts from Castle Hill and Toongabbie and is often referred to as the ‘Battle of Vinegar Hill’. There are many accounts which focus on the reasons for the rebellion and the main protagonists but perhaps less well known is the role of ‘Dorothy Mount’ a large hill in Toongabbie, just on the outskirts of Parramatta.
It was here that conspirators agreed to meet to await the torching of Elizabeth Farm and other properties which would be the signal to descend upon Parramatta and capture its arms and supplies. However things turned out badly for the rebels and instead the slopes of ‘Dorothy Mount’ became the site of the first rout of the rebels before the final act was played out at ‘Vinegar Hill’ (near Rouse Hill).
Initially the plot was kept a close secret with scarcely a whisper escaping in the days leading up to the revolt; remarkable in the extreme considering well over 300 convicts knew of the password ‘St. Peter.’ In other ways lack of coordination and poor communications meant it was doomed to fail.
The uprising started at Castle Hill during the dark of the night on Sunday 4 March, 1804. It was then that one of the houses in the little settlement was set alight, this being the signal for the insurgents to run through the camp plundering houses in the search for arms and alcohol. A fatal flaw in the plan soon became evident as the men drank alcohol and after finding a government official who had flogged them wasted time taking turns to inflict their own punishment on the unfortunate man.
Instead of making their way to Parramatta as planned this delay meant they lost the element of surprise as the watchman at Castle Hill had by this time escaped and raised the alarm in the tiny garrison at Parramatta. And by midnight Governor King at Sydney had also been alerted and 140 marines from HMS ‘Calcutta’ drafted into service to defend Sydney the town. After securing the town Governor King set off for Parramatta with around 40 men under the command of Major Johnson.
Johnson’s forces arrived at Parramatta in the early hours of 5 March and after resting at the local barrack marched off along Toongabbie road to intercept the rebels. It was now that his group of some 40 men came across a group of some 230 rebels gathered at the height of ‘Dorothy Mount’. After debating what tactics he should employ Johnson attacked the hill only to find the rebels had already decided to retreat leaving the summit empty. Thus ended the ‘Battle of Dorothy Mount’ and the final part of the tragic tale began to unfold as Johnson pursued the rebels.
After about ten miles Johnson’s exhausted men were slowing down and Johnson sent a trooper, Thomas Anlezark, with a horse and white flag to parley with the insurgents and try to slow them down. When he returned having had some success Johnson then sent another man Mr. Dickson, a Roman Catholic priest, to slow them down further. While this had brought Jonson more time his troopers were still too far behind the rebels and finally Johnson himself rode off with Anlezark.
Coming across them near ‘Vinegar Hill’ he waited until he was within a few yards of the rebels and then called out commanding them to HALT! When they stopped and turned the sight of this officer with only one trooper challenging them seems to have curiously impressed the rebels who were not to know there were only some 30 or so men in Johnson’s reserve. Two of the rebel commanders came forward to talk to the major who, after some parleying, clapped his pistol to the rebels head while the trooper seized the other commander. The delaying tactics appear to have worked for it was then that the rest of Johnson’s party arrived and although outnumbered successfully engaged the rebels, killing 12, wounding 6, and taking 26 more prisoner.
References: The Cumberland Argus and Fruitgrowers Advocate (Parramatta, NSW : 1888 – 1950), Wednesday 10 June 1908, page 2 National Library of Australia http://nla.gov.au/nla.news-article85983206 Arundel, J., Castle Hill, Journal and Proceedings of the Parramatta District Historical Society, Volume 1, 1918 Silver, L. M., The battle of Vinegar Hill, Doubleday, 1989.  Silver, L. M., The battle of Vinegar Hill, Doubleday, 1989, p.88  Silver, L. M., The battle of Vinegar Hill, Doubleday, 1989, p. 101  Silver, L. M., The battle of Vinegar Hill, Doubleday, 1989, p. 100