Chronology:
1794:
The first land grants were made in the Hawkesbury area to 22 emancipists in response to the need for additional agricultural land. By the end of 1794, over 100 grants were made in the region between present-day Windsor and Pitt Town. A government store, soldiers' barracks, granary, and government cottage were established at Green Hills (later known as Windsor) to service the settlement.

1794:
A road was established between the Green Hills/Hawkesbury area and the older settlement at Parramatta. The road amounted to a track, suitable for travel by horseback or foot. The road traversed the Government Domain at Parramatta and approached the Government Farm at Toongabbie.

1797:
Governor Hunter ordered landholders to undertake road improvements along the Hawkesbury Road, including widening the road to 20 feet. (This is the date for the creation of the Windsor Road as a carriageway.)

1802:
A bridge was constructed at a new South Creek crossing of the Windsor Road, financed by tolls, and replacing the previous punt crossing further east. The current road alignment at South Creek dates from this time. The earlier road alignment, leading to the punt crossing, is reflected in the alignment of the present day Hawkesbury Road.

1804:
Convicts from the government farm at Castle Hill revolted and were confronted by military forces near Rouse Hill. The battle came to be known as the Battle of Vinegar Hill after a 1798 uprising in Ireland against British rule. The soldiers were able to apprehend the rebels by quickly travelling via the Old Windsor Road, which was the key to the containment of the rebellion.

1805:
Surveyor James Meehan surveyed an alignment between Parramatta and Kellyville which became the basis for the (New) Windsor Road in 1813. A committee was formed to collect funds for the upkeep of the colony�s two main roads: Sydney to Parramatta, and Parramatta to Windsor.

1806:
Surveyor Grimes' map of 1806 shows the road from Parramatta to Green Hills (the Old Windsor Road) and from Prospect to the Cowpastures.

1810:
Governor Macquarie described the Windsor Road as "scarcely intitled [sic] to that name...in so bad a state of repair as to be scarcely passable." Later in the year, Macquarie established five towns along the river: Windsor, Richmond, Pitt Town, Wilberforce, and Castlereagh. A contractor, James Harrex, was engaged to build a new turnpike road between Parramatta and Kellyville, following Meehan's 1805 alignment via Castle Hill. This new alignment would avoid the hilly section (referred to by Governor King in 1803 as "the Seven Hills") of the original (Old) Windsor Road. The new alignment also enabled a more direct route to the Hawkesbury from Sydney. Most importantly, the new route avoided the newly-proclaimed Domain at Government House, Parramatta, and was part of Governor Macquarie's extensive plan for the improvement of Government House and its landscape setting.

1812-1813:
Upon the failure of James Harrex to complete the new road works, John Howe took over and completed the contract, which included the construction of 70 bridges. The new road was 32 feet wide and alignment stones marked the carriageway.

1810s:
Governor Macquarie introduced a toll system on the Windsor Road with toll gates north of Parramatta and south of Rouse Hill.

1816:
Land granted to Richard Rouse who built Rouse Hill House and moved in between 1818 and 1825. Rouse also constructed a toll house opposite.

1824:
A regular passenger coach service between Parramatta and Windsor commenced; however, the poor condition of the road caused the coach service to be suspended in the late 1820s. Complaints about the poor condition of the Windsor Road continued in the following decades. By the 1830s, passenger and mail coach services were established. 1826-1832 Governor Ralph Darling held an ambition for the colony�s roads to be developed along the concept of the English system of "great roads."

1827:
Newspaper report on "an outbreak of bushranging on the road between Sydney and Windsor. Several vehicles have been stopped and the passengers stripped of all valuables." Escaped convict, 'Bold' Jack Donohoe, described in 1830 as "the most notorious of the bushrangers currently operating in New South Wales," got his start robbing bullock drays on the Windsor Road. Donohoe is remembered as the last of the convict bushrangers and the first of the bushrangers to be romanticised in bush ballads.

1833:
Windsor Road was proclaimed as a Main Road under 4 Wm IV No 11, gazetted 11 September 1833, to be maintained at public expense.11 The Old Windsor Road was declared a Parish Road. 1835 A toll house, the second on the site, was constructed at the South Creek crossing near Windsor.

1830s:
The deteriorated condition of the Old Windsor Road rendered it "impassable" in sections, and the options of either repairing and re-opening the Old Windsor Road or creating a new road alignment were debated. The alignment stones along the Old Windsor Road may date from this period.

1830s-40s:
The No. 12 Road Gang, a convict gang, was assigned to maintain the Windsor Road, however lack of men and ineptitude of the overseer compromised were complained of in correspondence by the Roads Branch of the Surveyor General's Department.

1849:
The Windsor Road Trust was formed to oversee maintenance of the Windsor Road. Convict labour carried out maintenance in the previous two decades to the establishment of the Windsor Road Trust.14 Responsibility for the road between Vinegar Hill and Windsor was charged to the Windsor Road Trust, while from Vinegar Hill to Parramatta, responsibility for maintenance of the road was under the Parramatta Road Trust.

1853:
Fitzroy Bridge constructed across South Creek at Windsor, replacing the earlier Howe's Bridge.

1864:
Steam railway extended from Penrith to Richmond via Windsor.

1867:
Factors including the 1867 flood of the Hawkesbury River, the opening of land west of the Blue Mountains brought about by the railway in 1869, and the onset of the rust disease which affected the area's wheat crops combined to bring about the end of the Hawkesbury's role as Sydney's 'breadbasket.' Maize and vegetable crops replaced wheat farming, and in the 1880s, farmers in the Hawkesbury Valley turned to orcharding.

1885:
Surveyor Mackenzie surveyed the Old Windsor Road for the Surveyor General.

1920s:
Dairying and poultry farming industries took hold in the Hawkesbury Valley. Orcharding continued to take place along the roads in areas such as Baulkham Hills area.

1924:
The Department of Public Works used water-based macadam in reconstructing the Windsor Road near Rouse Hill. A bitumen coating was laid down in 1925-6, and renewed in 1928-9. Water-based macadam was an improved road surface treatment necessitated by the rapid rise of the motor vehicle.

1928:
Windsor Road, together with Bells Line of Road and the Darling Causeway was announced as Main Road 184 on 22 May.

1940s:
Cutting and filling of the Old Windsor and Windsor Roads was reportedly undertaken by the United States military to prepare evacuation routes should a Japanese invasion take place in Sydney.

1948:
Shoulders of the Windsor Road were widened to 22 feet to provide for anticipated traffic.

1981-1984:
High-level bridges constructed by the Department of Main Roads over Pye's Crossing and Johnston's Bridge. The last unmade section of Old Windsor Road was surfaced by Blacktown and Baulkham Hills Councils

Written Clive Lucas Stapleton 2005 Windsor and Old Windsor Roads Conservation Management Plan.

*Historical Significance The alignment (route) of the original Hawkesbury Road (now Old Windsor Road, and part of the Windsor Road) is of historic significance as the second road alignment to be established in the colony of NSW. The alignment influenced human activity in the region from its establishment in 1794, related to the earliest phase of expansion of settlement beyond Sydney and Parramatta. The alignment defined aspects of the settlement pattern (such as the laying out of grants and the consolidation of services at Green Hills) and provided the region's primary overland transport route, vital to the settlement of the north-western Cumberland plain. The re-alignment of the Windsor Road in 1812-1813 (after the foundation of the Macquarie Towns in 1810) is historically significant as a component of Governor Macquarie's vision for the orderly settlement of the colony, particularly for the Hawkesbury region and the Governor's Domain at Parramatta. The new alignment's avoidance of the hilly section of the original route provides evidence for the presence and naming of the 'Seven Hills' now known as the Hills District. The Windsor Road is part of the first turnpike system in the colony. The decline in status of the Windsor and Old Windsor Roads post-1850 reflects the corresponding decline in the Hawkesbury region's importance as Sydney's breadbasket.