Travels with my Ancestors #27: The rags to riches tale of the Roberts family story, Part Three
“The old toll bar at Dog Trap Road,
c. 1840s,” Reference Number: LSP00369.
This is Part Three of the epic story of my ancestors, William Roberts and Jane Longhurst.
You can find Part One here and Part Two here.
So far we have followed William and Jane as they survived their voyage to NSW on convict transports, earned their freedom and began to make new lives in Sydney. William had been granted land in Sydney Town and at Bondi. Their colonial stars were on the rise.
Part Three: Thriving
William’s first recorded job under the new Governor, Lachlan Macquarie, was in 1810, working on stone bridges in Sydney, for which he was paid £100.[i]
That same year, he and Jane were married at St Philip’s church in Sydney.[ii] Jane had already given birth to a daughter and three sons (including twins Charles and Thomas, my 3 x great-grandfather) and she was heavily pregnant with their fourth son, Richard, on the wedding day.[iii] There were few among their fellow emancipists who’d cast judgement on a family born out of wedlock, although the clergy and authorities continually urged the colonial population to formalise their unions.
William’s work was favoured by the Governor. Macquarie was appalled by the state of the roads and dwellings in the ramshackle areas of Sydney Town that had sprung up in those earlier years, and ordered householders to take responsibility for the cleanliness and repair of the streets outside their homes. He threatened to impose an annual tax on anyone not doing so, and recommended someone who could help with any repairs that were needed:
William Roberts having rendered much satisfaction to His Excellency by his substantial repair of George Street, he is recommended to the consideration of the inhabitants as well qualified to make good the repairs now required.
By Command of His Excellency The Governor.[iv]
Three years later came William’s most lucrative contract yet. He was appointed by the Governor to work under superintendent Thomas Moore, of Liverpool, to build a new road and bridges joining the existing Parramatta Road (at present-day Ashfield) to the new settlement of Liverpool, the first planned township settled by free arrivals.[v] Settlers needed better access to and from farms; securing food resources was always a preoccupation of colonial authorities and safe and reliable routes for grain and crops were essential.
Convict road gangs did the hard work of shovelling dirt, breaking stones, cutting trees; William was supervisor and responsible for the work being completed on time and to a budget. The new road was known then as ‘Dog Trap Road’ (because of the many dingo traps set nearby to protect settler livestock). It was renamed decades later as ‘Woodville Road’.
What an extraordinary turnaround: from labourer, to convict, to engineer, project manager and supervisor of convicts. When he’d galloped away on that gelding from Wootton Hall, he could not have imagined that he would end up as a respected road builder in NSW, twenty-seven years later. There must have been huge satisfaction, too, in knowing that, while on the population and convict muster records, his trial at Warwick and arrival on the Neptune were always listed, by the 1810 record he was described as a ‘landholder.’ [vi] By 1816 he had added ‘trader’ to his occupations.[vii]
William began work on the Liverpool road in 1813. The project included constructing bridges as well as creating a proper road from the bush tracks that had been used to that point.
It’s likely that at least some of those tracks had been established by the Cabrogal/Cahbrugal people of the Dharug nation, or those of neighbouring Tharawal or Gundungurra/Gandangana groups, as they travelled through the region on tribal business. It’s very unlikely that the men labouring on the new road would have given that possibility any thought, unless they glimpsed or met Aboriginal people while at their work.
When the road was completed, the Governor travelled along its length by carriage and reportedly expressed much satisfaction with the general line and performance of that important work.[viii]The new road was 24 km in length and included 27 new bridges.[ix]
With the success of this first major project, William was given many more contracts by Macquarie. He oversaw the extension of the Parramatta Road to Windsor, as well as roads and bridges at Airds, Minto, Bringelly, and the Cowpastures.[x]
Between 1813 to 1819 he was paid £8,000 in cash and £1,000 in spirits for the work he’d completed for the Governor.[xi]
In addition to all this activity he was busy with his farm and hotel businesses.
The Land and Stock Books of 1818 recorded him farming 50 cleared acres of land, on which he produced wheat, maize, barley and oats. He also raised 30 hogs, 30 horned cattle and owned a horse.[xii] Did he smile to himself when he took ownership of that last animal? Such a purchase would have once been nothing but a pie-in-the-sky dream. He had once stolen a horse; now he could buy one outright.
He opened the King’s Arms Hotel in Hunter Street, Sydney; Jane assisting with the many tasks involved in providing accommodation, food and drink to patrons. She would do so while tending to the care of their growing family. Benjamin (known as James) was born in 1816, the youngest of eight; his elder siblings Ann (known as Jane), William, twins Charles and Thomas, Richard, Elizabeth, and Joseph.[xiii]
The King’s Arms was a two-storey weatherboard building on a large corner block. The Roberts established an orchard and a kitchen garden to supply produce for the hotel’s meals.[xiv] They ran a tight ship at the pub, again winning the Governor’s favour. When Governor Macquarie was attempting to grapple with the fact that the settlement was awash with liquor, he had made the following proclamation:
Government House, Sydney, 16th February 1810
The very great and unnecessary Number of Licenced Houses for Retailing Wines and Spirituous Liquors that have hitherto been allowed to exist in the town of Sydney and adjacent districts, cannot fail of being productive of the most mischievous and baneful Effects on the Morals and Industry of the lower part of the Community, and must inevitably lead to a Profligacy of Manners, Dissipation, and Idleness. In view, therefore, to check these Evils, as well as in the Hope of awakening Sentiments of Morality, and a Spirit of Industry amongst the lower Orders of the People, His Excellency the Governor had deemed it his indispensable Duty to make a Reduction of the Number of Licenced Houses for Retailing Spirits…[xv]
He restricted the number of licensed public houses to twenty, closing fifty-five in the process and imposing a hefty fine of £20 for anyone found selling liquor outside these restrictions.
William and Jane’s establishment was on the list of favoured publicans in Sydney Town—along with the likes of Mary Reiby, a fellow emancipist who became one of the wealthiest women in the colony.
They also opened an inn or halfway house on the Liverpool Road, catering to travellers needing to stop for a meal, to rest horses, or an overnight stay.[xvi] If Jane worked here, in the kitchen or at the bar, she would have had convicts—a scullery maid and cook—to assist her.
Sometimes she too, must have marvelled at how fate had changed her lot from her time on a transport ship, to a woman with money and resources. Their stars had well and truly risen.
~
The town around them was changing under Macquarie’s public improvement program. Convicts laboured on handsome buildings such as the Hyde Park Barracks, St James Church and a new general hospital; charity schools were established in Sydney and outlying districts. The Governor acted to stabilise the colony’s wavering currency and established the first bank, the Bank of New South Wales, which was financed by private subscription and opened in 1817.[xvii]
These measures were helpful to businesspeople like the Roberts. Wealthy traders built warehouses along the wharves of Sydney Cove; shopkeepers, publicans, and essential tradespeople like tanners or blacksmiths built up flourishing businesses. The straggling settlement that William had seen when he first arrived was being transformed.
Hyde Park Barracks (L) ; The Courthouse and St James’ Church Hyde Park Sydney (R)
Source: Mitchell Library, SL NSW
Their circumstances were in accord with Governor Macquarie’s desire to see emancipists become part of the fabric of the colony, working to establish wealth and a future for themselves and their families. They were doing exactly as the Governor wanted all settlers to do: clear and cultivate land, growing produce along with a new generation of colonial-born youngsters to occupy and make productive this offshoot of the British Empire. Their children were thriving; unlike Jane’s own mother, she did not have the all-too-common experience of seeing any of her babies die. They lived in comfortable surroundings and never had to worry about where the next meal would come from.
Despite their difficult start, their life together was on an upward trajectory. They must have reflected on the years since they had each stood in the docks and heard the words transportation across the seas. They could not have guessed what awaited them in far-away New South Wales. Now, they had achieved a level of independence and prosperity that would have been unimaginable in Warwickshire or Surrey. Neither were literate, but if they could have written to their families back in England, what stories they could have told!
Among the free settlers and military in New South Wales were those who called themselves ‘exclusives’ and who were in bitter opposition to these developments. To them, convicts could never rid themselves of the stain of their criminal past and should not be afforded the same rights and privileges as those who had come free to the colony.
The Roberts were living at the interface of these conflicting views.
William & Jane’s stories will be continued in my next post.
[i] NSW Colonial Secretary’s Papers 1788-1856 Series: NRS 898; Reel or Fiche Numbers: Reels 6020-6040, 6070; Fiche 3260-3312. Via Ancestry.com, accessed 3 Dec 2025
[ii] Australia Marriage Index, 1788-1950, William Roberts & Jane Longest, 3 April 1810. Via Ancestry.com, accessed 3 Dec 2025
[iii] Australia & New Zealand Find-a-grave Index, Ann Roberts Levey; https://www.findagrave.com/memorial/249401714/ann-levey?_ Accessed 7 Dec 2025
Fairfax Media; Pyrmont, New South Wales, Australia; Year Range: 1841 – 1842; Australia, Newspaper Vital Notices, 1841-2001, Death notice for William Henry Roberts 1841. Via Ancestry.com, accessed 7 Dec 2025.
Australia, Births and Baptisms, 1792-1981, Baptism of Thomas Grenville Roberts 1807, FHL Film No 993949.
Via Ancestry.com, accessed 7 Dec 2025; Global, Find a Grave Index for Burials at Sea and other Select Burial Locations, 1300s-Current, Charles Roberts 1865, https://www.findagrave.com/memorial/263496717/charles-roberts?_ Accessed 7 Dec 2025; Australia Birth Index, 1788-1922, Richard Roberts b 1810. Via Ancestry.com, accessed 7 Dec 2025
43 New South Wales, Australia, Colonial Secretary’s Papers, 1788-1856, Series: NRS 898; Reel or Fiche Numbers: Reels 6020-6040, 6070; Fiche 3260-3312. Via Ancestry.com, accessed 6 Feb 2026
[v] NSW Colonial Secretary’s Papers 1788-1856, Series: NRS 898; Reels 6020-6040, 6070; Fiche 3260-3312,
Via Ancestry.com, accessed 7 Dec 2025
[vi] State Records Authority of New South Wales; Kingswood, New South Wales, Australia; Title: Muster of Prisoners in the Colony, 1810-1820; Volume: 4/1237. Via Ancestry.com, accessed 9 Dec 2025
[vii] New South Wales, Australia, Settler and Convict Lists, 1787-1834, Class: HO 10; Piece: 3. Via Ancestry.com, accessed 9 Dec 2025
[viii] 1904 ‘The Great South Road’, The Sydney Morning Herald (NSW: 1842 – 1954), 25 June, p. 7.
Via Trove, http://nla.gov.au/nla.news-article14661003. Accessed 9 Dec 2025,
[ix] https://www.visitsydneyaustralia.com.au/major-roads.html. Accessed 9 Dec 2025
[x] Michael Flynn, The Second Fleet: Britain’s Grim Convict Armada of 1790, p503
[xi] Michael Flynn, The Second Fleet: Britain’s Grim Convict Armada of 1790, p503
[xii] State Records Authority of New South Wales; Kingswood, New South Wales, Australia; Population musters, Dependent settlements; Series: NRS 1264; Reel: 1256. Via Ancestry.com, accessed 9 Dec 2025
[xiii] Australia, Births and Baptisms, 1792-1981 For Elizabeth Roberts 1812 https://familysearch.org/ark:/61903/1:1:XTCX-4XX, accessed 10 Dec 2025; Australia, Births and Baptisms, 1792-1981 for Joseph Roberts 1814, FHL Film Number 993949; For Benjamin James Roberts 1816 FHL Film Number 993949. All via Ancestry.com, accessed 10 Dec 2025
[xiv] 1882 ‘Old And New Sydney.’, The Sydney Morning Herald (NSW: 1842 – 1954), 27 November, p. 11
Via Trove http://nla.gov.au/nla.news-article13524564, accessed 13 Dec 2025
[xv] Historical Records of NSW vol 7 (1810, 1811, 1812), pp289-290, via Trove, accessed 10 Dec 2025
[xvi] State Records of NSW, Colonial Secretary Index 1788-1825, Reel 6038; SZ759 p.342.
Via Ancestry.com, accessed 10 Dec 2025
[xvii] Commerce and trade | State Library of New South Wales (nsw.gov.au) Accessed 10 Dec 2025
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