Roads around Sydney
  The Government Stock Yard, north of Meurants Lane was established by 1800, the original road construction or it may have been part of the overall upgrade ordered by Governor Macquarie in 1809

The branch of Windsor Road Linked to the Great North Road via Castle Hill (known as Windsor Road to distinguish it from Old Windsor Road) was established around 1812 . It appears that this newer branch of Windsor Road was developed to avoid crossing the Government Domain at Parramatta, resulting in a more direct route to Sydney. It also increased the road haulage capacity over the length of both Windsor Roads

However it was the Old Windsor Road which remained the principal route for settlers and the movement of produce. The condition of both roads was a source of much complaint. Despite Grimes assertions that it was a "very good road", Governor Macquarie thought differently, declaring shortly after his arrival that "the present road is scarcely intitled [sic] to that name. It is in so bad a state of repair as to be scarcely passable"

It is likely that in this section of Old Windsor Road by the time the Government Stock Yard was installed on the north side of Meurants Lane in 1800

Road upgrades undertaken by the residents in the region  in 1797 .

 
 
The economic depression of the 1840s contributed to the already inadequate funding for maintenance, let alone improvement. The first issue of the Hawkesbury Courier (11/7/1844) states that "the road from Windsor to Parramatta has long been in a disgraceful state." The Sydney Morning Herald gives the following description of the state of Old Windsor Road:

 

The poor horses were tried to the utmost by the deep ruts and almost interminable sloughs, the soft yellow clay ploughed by the narrow wheels and hollows of veriest mud. We passed several teams on the road struggling for existence...About midway a large load of hay was capsized in the centre of

the road and by the side of a hill, a dray full of grain had also upset. (23/6/1857