1788 to 1810
| 1788 | Auburn | Phillip, Hunter, Bradley and others explore by land and river from Homebush Bay along Duck river |
| 1788 | Camden | All the colony's cattle - four cows and two bulls - wander from Sydney settlement |
| 1788 | Baulkham Hills | Phillip, Collins and others view Hawkesbury and Blue Mountains from Castle Hill area |
| 1788 | Parramatta | Europeans explore Parramatta district; site at Rose Hill occupied |
| 1788 | Blue Mts | Blue Mountains was the traditional country of the Gundungurra who lived in the Burragorang Valley and the gorges of the southern Blue Mountains. The Dharug lived in the northern mountains, including on the main ridge |
| 1789 | Hawkesbury | Phillip explored and named Hawkesbury River |
| 1789 | Parramatta | Rose Hill packet, first vessel for Parramatta River trade, launched |
| 1789 | Parramatta | first wheat crop harvested at Rose Hill |
| 1789 | Blue Mts | Lt William Dawes crossed the Nepean and reached the vicinity of Faulconbridge-Linden |
| 1789 | Penrith | Captain Watkin Tench led an exploratory party from Parramatta which reached the Nepean River, named by Governor Phillip. |
| 1789 | Penrith | Ample evidence of Aboriginal activity along the banks of the Nepean river - hunting huts, marks on trees, possum traps and decoys for birds |
| 1790 | Parramatta | Town of Parramatta laid out |
| 1790 | Parramatta | First vice-regal country residence built at Parramatta |
| 1790 | Penrith | Nepean forded and tentative exploration in to the mountains. |
| 1791 | Parramatta | Rose Hill renamed Parramatta |
| 1791 | Parramatta | Toongabbie convict station formed |
| 1791 | Parramatta | James Ruse's grant issued |
| 1791 | Blacktown | Thirteen exconvicts granted land at base of Prospect Hill - the first major independent farming settlement? |
| 1791 | Parramatta | Toongabbie founded as a government farm in 1791 |
| 1792 | Auburn | Land grants to free settlers arriving on the Bellona give Auburn its earliest name - Liberty Plains. |
| 1792 | Northern LGAs | The line of Old Windsor Road was marked as early as 1792 and the road completed in 1794 |
| 1793 | Parramatta | Elizabeth Farm built |
| 1794 | Hawkesbury | 22 settlers established at junction of Hawkesbury and South Creek |
| 1794 | Hawkesbury | First track between Green Hills and Sydney - Old Windsor Road |
| 1794 | Parramatta | Road to Parramatta from Sydney built |
| 1794 | Blacktown | Matthew and Martha Pearce arrived as free settlers and were granted 160 acres which they called Kings Langley Farm. |
| 1795 | Camden | Runaway cattle discovered at the Cowpastures |
| 1795 | Baulkham Hills | first farm at Sackville Reach |
| 1795 | Blue Mts | Matthew Everingham's exploration of the Blue Mountains reached Mt Irvine or Mt Tomah |
| 1796 | Blue Mts | George Bass's travels along lower Burragorang Valley, almost reaching Kanangra Walls |
| 1797 | Auburn; Parramatta | Sydney to Parramatta road built |
| 1798 | Liverpool | First land grants in Liverpool on George's River at Chipping Norton |
| 1799 | Hawkesbury | First recorded flood at the Hawkesbury |
| 1799 | Baulkham Hills | Grant to Andrew McDougall at Baulkham Hills |
| 1800 | Baulkham Hills | Grant to George Suttor at Chelsea Farm, Baulkham Hills |
| 1801 | Hawkesbury | Andrew Thompson built first bridge over South Creek, Windsor |
| 1801 | Baulkham Hills | John and Elizabeth Macarthur acquire Bella Vista, Seven Hills |
| 1801 | Blacktown | Joseph Foveaux sold his farm and flocks in the district of Toongabbie to John Macarthur. This became Elizabeth Macarthur's Seven Hills farm - later known as Bella Vista. |
| 1802 | Southern LGAs | Caley traced the Nepean from Wallacia to Camden |
| 1802 | Baulkham Hills | Castle Hill Government Farm established as a convict farm |
| 1802 | Blue Mts | Ensign Francis Barrallier travels west from the Wollondilly River, almost as far as the Kanangra Plateau |
| 1802 | Blacktown | Governor King reserved a vast area (about 58,000 acres) at Rooty Hill between Eastern Creek and Rope's Creek for a government stock reserve |
| 1803 | Camden | John Warby appointed government herdsman at the Cowpastures |
| 1803 | Parramatta | St Johns Church Parramatta opened |
| 1803 | Parramatta | Coach service established between Sydney and Parramatta |
| 1803 | Parramatta | Government Water Mill built on Parramatta River |
| 1804 | Baulkham Hills; Blacktown | A convict uprising at Castle Hill by Irish convicts who marched on Parramatta, then back to the Hawkesbury looking for supporters. Their military encounter with the New South Wales Corps was known as the Battle of Vinegar Hill. |
| 1804 | Hawkesbury | First vessel built on the Hawkesbury - Jonathan Griffiths of Richmond. |
| 1804 | Liverpool | Grant to Eber Bunker at Collingwood |
| 1804 | Liverpool | Grant to Thomas Moore at Moorebank |
| 1804 | Camden | John Macarthur granted 5,000 acres by Lord Camden, which he selected at the Cowpastures. |
| 1804 | Baulkham Hills | Building of first flour mill at Arndell's Cattai farm |
| 1804 | Parramatta | First publicly owned brewery began operations in Parramatta |
| 1804 | Blue Mts | George Caley travelled as far as Mount Banks (now Mount King George) |
| 1805 | Camden | Macarthur moved his flocks to Camden Park (named after Lord Camden, Secretary for Colonies) and established a hut on the Benkennie ridge (later Belgenny), away from the floods. - slab hut, bark roof. Remained nucleus of working farm at Camden |
| 1806 | Penrith | Grime's map of the colony indicated there was no road westward from Parramatta and Prospect, even though there were settlers on the small farms of South Creek and the eastern bank of the Nepean. |
| 1806 | Penrith | Land grants by Bligh to the family of Governor King established a substantial network of landholdings north of the Western Road between Prospect and Penrith, reinforced by later grants to other family members. |
| 1807 | Auburn | John Blaxland takes up grant called Newington on Parramatta River |
| 1807 | Auburn | Salt making at Newington under Mr Rutter |
| 1807 | Baulkham Hills | First commercial sale of oranges from Baulkham Hills |
| 1809 | Hawkesbury | Ebenezer Chapel built - the oldest Presbyterian Church in Australia |