George Street began from the north leg of the first road and travelled south along 'the only possible route along the fringe of the west side of the ridge running alongside the Cove'. It was soon to become the principal street of the town. Previously known as High Street, Springrow and Sergeant-Major's Row, it was re-named George Street by Macquarie a few weeks after its first toll gate was opened. In its early days it was far from straight and meandered through a motley group of buildings. This famous bullock track served Australia's first settlement, first hospital, first customs house, first gaol, first theatre, first market, first brickworks and first cock-fighting arena.

Meanwhile, Rose Hill, later called Parramatta, had been settled by using boats to sail up the Parramatta River. The first road of any significant length was a 25 km cleared track cut through thick bush between Sydney and Parramatta between 1789 and 1791. The new road took some eight hours to walk and its non-official use was discouraged. It was largely used by foot traffic and the first horse-drawn cart did not negotiate the road until 1794. The road was first upgraded in 1797, when it was widened to 6 m and a bridge over the Duck River was completed, which was said 'to be capable of bearing any weight'. In 1798, severe rains rendered the road impassable. By 1806 the rutting on the road was so bad that a notice was posted in the Sydney Gazette requiring all vehicles using it to take with them a load of broken bricks from the brickworks at Brickfield Hill. These were to be dropped in places nominated by the Overseer of Roads.

A romantic view of the Parramatta road was published in 'The Monthly Magazine' 1st Sept. 1809:

A large road leads from Sydney to Parramatta; it is not paved but is made and kept in good condition. It is almost wide enough for three carriages to pass abreast and bridges have been thrown over such parts of it as are interrupted by waters -this grand road appears from the distance like an immense avenue of foliage and verdure.

After reconstruction of the Parramatta Road in 1811 toll gates (bars) were placed in George Street just past Brickfield Hill, although the House of Commons did not legalize them until 1819.

Parramatta Road was subsequently roughly and slowly paved. According to Newell, Prospect dolerite was used, but Professor O. G. Ingles of the University of N.S.W. has claimed in a private communication that the widespread use of dolerite and other igneous rocks in the latter half of the 19th century misled subsequent commentators. He states that his inspection of early roads has only indicated the use of sandstone and quotes testimony of Major Druitt in 1819 that roads were being constructed from soft sandstone and clay, with improvements coming from the use of ironstone, shale and gravel. Although the Sydney sandstones proved excellent for building purposes, their softness has always rendered them poor road-making materials.

Australian Academy of Technological Sciences and Engineering