1810 - 1849
| 1810 | Liverpool | Town of Liverpool founded by Macquarie and named after Robert Banks Jenkinson, Second Lord Liverpool, English prime minister |
| 1810 | Hawkesbury | Death of Andrew Thompson - first recorded burial in St Matthews Church of England cemetery |
| 1810 | Hawkesbury | Macquarie's visit to the Hawkesbury - creation of five towns of Windsor, Richmond, Wilberforce, Pitt Town and Castlereagh |
| 1810 | Hawkesbury | Macquarie's plans for the towns also included instructions on the houses - to be substantial buildings of brick or weatherboard - all at least nine feet high. |
| 1810 | Campbelltown | Macquarie toured district and named it Airds after his wife's home in Scotland. |
| 1810 | Campbelltown | Campbellfield at Minto granted to William Redfern |
| 1810 | Liverpool | Eber Bunker built Collingwood - still standing |
| 1810 | Liverpool | Macquarie founded the town of Liverpool. naming it after the Earl of Liverpool, then the British Secretary of State for the Colonies |
| 1810 | Baulkham Hills | Castle Hill Lunatic asylum founded |
| 1810 | Camden | Governor and Mrs Macquarie camped at Belgenny near the Macarthur hut |
| 1810 | Penrith | First surveyed town in Penrith area was Castlereagh, established by Governor Macquarie |
| 1810 | Penrith | Large land grants made in Mulgoa Valley with most of the valley granted by 1816. |
| 1811 | Campbelltown | Lachlan Vale, Appin granted to William Broughton |
| 1811 | Liverpool | Construction work on a schoolhouse and military barracks. |
| 1811 | Baulkham Hills | Castle Hill farm converted to lunatic establishment by Governor Macquarie |
| 1812 | Camden | Grants issued for Macquarie Gove (Hassal), Wivanhoe (Cowper); Birling (Lowe) |
| 1812 | Camden | Government stock yards established at Cawdor |
| 1813 | Penrith | Blaxland, Lawson and Wentworth set out from their Nepean landholdings to find a route over the Blue Mountains |
| 1813 | Blue Mts | Evans surveyed road over mountains and Cox built the Great Western road to Bathurst |
| 1813 | Hawkesbury | At Richmond, a school house was erected and used as a chapel on Sundays. |
| 1813 | Blue Mts | Blaxland, Lawson and Wentworth succeed in finding a route over the Blue Mountains |
| 1814 | Liverpool | Road from Sydney to Liverpool completed |
| 1814 | Blue Mts | George Evans surveyed the route of Blaxland, Lawson and Wentworth and travelled further west |
| 1814 | Penrith | Government stockyard at Emu Plains on reserved land which became a nucleus for a police and military presence |
| 1815 | Blue Mts | William Cox supervised a road gang which constructed a road over the mountains as far as Bathurst |
| 1815 | Blue Mts | Governor Macquarie travelled over the new road to Bathurst, naming Springwood and Blackheath en route |
| 1815 | Camden | Grants issued for Kirkham (Oxley); Denbigh (Hook), Harrington Park (Campbell); Orielton (Lord) |
| 1815 | Penrith | Work on road linking Parramatta and Emu Plains was stimulated by Evan's road across the Blue Mountains, as Macquarie returned on the new Western road still under construction. Quickly established as main route. |
| 1815 | Blacktown | Macquarie authorised construction of a two storey brick house for the superintendent of government stock at Rooty Hill. It was called Government House. |
| 1816 | Auburn | Blanket and tweed manufacturing at Newington |
| 1816 | Campbelltown | Aboriginal conflict at Campbelltown |
| 1816 | Campbelltown | John Warby received land grant at Campbelltown |
| 1816 | Camden | Captain Wallis attacked native camp near Broughton's farm Appin - Appin massacre |
| 1816 | Parramatta | Native Institution, a school for Aboriginal children, established at Parramatta under William Shelley |
| 1816 | Blacktown | Macquarie granted land to Aboriginal guides Colebee and Nurragingy |
| 1817 | Hawkesbury | Foundation stone of St Matthews church laid by Macquarie |
| 1817 | Penrith | First Methodist chapel in Australia built at Castlereagh |
| 1817 | Camden | Road from Sydney to Liverpool completed |
| 1817 | Liverpool | Glenfield house built by Charles Throsby |
| 1817 | Baulkham Hills | Solomon Wiseman's grant at Wiseman's Ferry |
| 1817 | Penrith | Weatherboard court house, lock up and travelling stock paddock formed core of new village of Penrith in 1817, on higher ground than the river ford. |
| 1818 | Hawkesbury | Cox built new road from Prospect to Richmond, latter called Blacktown-Richmond Road |
| 1818 | Hawkesbury | Rouse Hill House built by Richard Rouse |
| 1818 | Liverpool | Foundation stone laid for St Lukes church |
| 1818 | Parramatta | Female Orphan School opened at Parramatta |
| 1819 | Auburn | Limeworks at Newington |
| 1819 | Camden | Macquarie ordered a road to be constructed south from Liverpool for 75 miles (120kms) to the limit of known settlement. |
| 1819 | Penrith | Government resisted settlement west of Nepean River until 1819 when Emu Plains Agricultural Farm established as a convict establishment. |
| 1819 | Blacktown | William Minchin granted land west of Rooty Hill which he called Minchinbury |
| 1819 | Blacktown | William Cox built a second road to the Hawkesbury in 1819 - the Blacktown -Richmond Road. It was remade in 1822 |
| 1820 | Hawkesbury | Convict barracks built at Windsor |
| 1820 | Campbelltown | Macquarie returned to southern district and established town called Campbelltown after his wife's maiden name |
| 1820 | Campbelltown | Capt Brooks takes up residence at Denham Court |
| 1820 | Parramatta | New Female Factory constructed outside the town. |
| 1821 | Campbelltown | School at Macquarie Fields opened by Rev Thomas Reddall |
| 1822 | Liverpool | Foundations laid for Liverpool hospital, intended to serve wide area because of its good air and water. |
| 1822 | Baulkham Hills | Pye's Lamb and Lark Inn, Baulkham Hills |
| 1822 | Parramatta | First Agricultural Society in Australia formed at Parramatta |
| 1822 | Parramatta | Governor Brisbane's observatory built at Parramatta |
| 1822 | Blacktown | Construction of road from Prospect to Richmond (the Blacktown Road ) was the first road built on the new principles of McAdam - a macadamised road |
| 1823 | Hawkesbury | Windsor convict barracks converted to a hospital |
| 1823 | Hawkesbury | Archibald Bell established alternate route over mountains from Richmond |
| 1823 | Campbelltown | St Peters Church Campbelltown opened |
| 1823 | Blacktown | Native Institution moved from Parramatta to Richmond Road, area becoming known as Black town |
| 1823 | Blue Mts | Archibald Bell found an alternative route over the mountains through Kurrajong |
| 1823 | Blue Mts | Collits's Inn opened at the foot of Mount York. Pierce Collits was an emancipist constable from Penrith |
| 1823 | Penrith | Sir John Jamison built Regentville, a magnificent mansion that drew the attention of many colonial visitors |
| 1824 | Camden | Hume and Hovell set out from Minto and Appin to explore country south to Port Phillip Bay |
| 1824 | Blacktown | Bungarribee - a grant for John Campbell |
| 1825 | Fairfield | James Busby, pioneer viticulturalist, planted grape vines at Orphan School estate. |
| 1825 c | Holroyd | Kenyon's Road built by convicts from Mays Hill to Prospect Creek |
| 1826 | Fairfield | Survey of Male Orphan School site |
| 1826 | Fairfield; Parramatta; Liverpool | Parramatta to Liverpool road - now Smithfield Road - in use as main route to south. |
| 1826 | Hawkesbury; Baulkham Hills | Great Northern Road built to link Sydney and its region to the Hunter Valley |
| 1826 | Campbelltown | Frederick George James Fisher murdered at Campbelltown |
| 1826 | Baulkham Hills | Castle Hill Lunatic asylum closed |
| 1826 | Baulkham Hills | Bridge at Darling Mills built (Broken Back Bridge) |
| 1826 | Blacktown | Australia's first native born poet - CharlesTompson - published his book of verses. His home was Clydesdale. |
| 1827 | Baulkham Hills | first punt at Wiseman's ferry |
| 1827 | Blue Mts | The Weatherboard Inn opened at Wentworth Falls and for many years the area was known as Weatherboard |
| 1828 | Hawkesbury | Hobartville built by William Cox jr at Richmond |
| 1828 | Camden | Heber Chapel at Cobbitty dedicated |
| 1828 | Blacktown | Rooty Hill stock reserve, reduced in area to about 8,000 acres closed and transferred to Church and School Corporation. |
| 1830 | Fairfield | Richard Sadlier, master of Male Orphan School, made first wine from grapes grown in Fairfield district. |
| 1830 | Liverpool | Hospital completed |
| 1830 | Blue Mts | The Pilgrim Inn at Blaxland was first licensed. |
| 1831 | Blue Mts | The Valley Inn at Valley Heights licensed |
| 1832 | Auburn | Blaxland's stone mansion house, Newington completed |
| 1832 | Parramatta | King's School established at Parramatta |
| 1832 | Blue Mts | Victoria Pass opened as alternative route to steep descent of Mount York |
| 1832 | Camden | German vignerons working on Camden Park estate |
| 1832 | Camden | Camden Park House built on ridge near earlier Belgenny. |
| 1833 | Fairfield | Early alignment of roadway which later became Horsley Drive in use |
| 1833 | Fairfield | Horsley Park developed by Blanche Weston, daughter of grantee Col George Johnston |
| 1833 | Campbelltown | First water reservoir built at Campbelltown |
| 1833 | Blue Mts | David Lennox completed construction of bridge at Lapstone Hill |
| 1836 | Fairfield | Portion of Orphan School estate sold to John Ryan Brenan |
| 1836 | Hawkesbury | Hawkesbury Benevolent Society established asylum for sick and poor |
| 1836 | Campbelltown | Mt Gilead windmill built by Thomas Rose |
| 1836 | Liverpool | Lansdowne Bridge, designed by David Lennox, opened by Governor Bourke. 1,000 convicts worked on its construction. |
| 1837 | Campbelltown | James Ruse, pioneer of wheat farming, died and buried at St Johns cemetery |
| 1837 | Penrith | Bishop Broughton chose a site at Penrith for a new church - St Stephens (even though there was little there to support such a large church at that time). Development seems to have followed the church. |
| 1839 | Parramatta | Lennox Bridge, Parramatta, completed |
| 1840 | Fairfield | Fairfield was named by Captain John Horsley after a place in Somerset, England. |
| 1840 | Campbelltown | Macquarie Field house built for John Hosking |
| 1840 | Campbelltown | Glenalvon House built for Michael Byrne |
| 1840 | Western LGAs | Transportation of convicts ceased |
| 1840 + | Camden | As better country found for sheep, local agriculture turned to wheat, maize, millet and later dairying |
| 1840 | Camden | Extensive wheat growing in Camden district, and associated flour milling, until devastated by rust in 1861 |
| 1840 | Camden | Township site surveyed and offered for sale as half acre allotments following death of John Macarthur, who had resisted suggestions of a town |
| 1841 | Fairfield | Smithfield Market housing estate offered for sale. Based around cattle market and wool market. Bad timing - depression |
| 1841 | Holroyd | Cattle sale yards established on Wentworth estate, east of Prospect Creek by William Fullaghar. Major cattle sale yards for metropolitan Sydney until opening of Homebush Yards in 1880s. |
| 1844 | Baulkham Hills | George Peat established ferry service across Hawkesbury River at Kangaroo Point. |
| 1846 | Auburn | John Blaxland dies at Newington |
| 1848 | Fairfield | German migrant Jacob Stein purchased land at Prospect Creek for vineyard, the first of a network of German vignerons. |
| 1848 | Parramatta | Female Factory converted to asylum, initially for destitute but by the 1850s as asylum for the insane |
| 1849 | Blue Mts | Toll gates established at Seventeen Mile Hollow (Linden) and Broughton's Waterhole (Mount Victoria) |