The Gaol Bridge was the first substantial bridge to join the southern and northern section of the new colony at Parramatta (although as James Jervis points out in his 1933 publication ‘The Story of Parramatta and District’, there had been an earlier bridge which connected the Government Farm with the original settlement, but this had been washed away).
This wooden Gaol bridge was constructed on the site of the Lennox Bridge and had a crossing span at Church Street which gave access between the town and the gaol. It also helped to open up access to the growing settlements to the north of Parramatta River.
Governor Phillip had planned for a large, magnificent town square to close the vista at the northern end of Church Street, next to the river. It can safely assumed that he planned future access across the river by a bridge at Bridge Street (the first bridge), and if there was probably to be a second bridge at the end of either Smith or Charles Streets.
Governor Hunter made no mention of a bridge in 1796 when he erected the first wooden gaol on the site in Prince Alfred Square but King mentions its existence when he commenced a new stone gaol in August 1802. To give access to the gaol, and the first Female Factory built on top of it, King decided to bridge the river at the end of Church Street.
The decking of the bridge was supported on ten sandstone piers. It was of timber and included a guard-rail or balustrade on either side that comprised drop posts with top and bottom rails with each section infilled with timber diagonals.
From the image made from the sketches done on the Dumant D’ville visit it appears as if the approaches to the northern end required extensive fill as the river bank was quite low. Foundations of the buildings on either side of the approaches, which are well below the road level, evidence this. James Houison’s Bond House, once on the site of David Jones’ Department Store, is known to have had two floor levels below the Lennox Bridge. The northern bank of shale made a good abutment for that end of the bridge and the height of the bank may still be seen.
Floodwaters in 1826 severely damaged three of the piers and, with one being rebuilt in late 1827 , the bridge managed to survive until the late 1830s. Even then it was declared as almost impassable. It was said that ‘even when a horse cantered over it, the bridge would shake. Stockmen told of cattle falling over the sides on being herded across the bridge, as apparently balustrading was missing. Piers supporting the two longer spans on the northern side were now missing and these spans had to be strengthened with trestles of hardwood posts which were braced with diagonals against the feet of the existing stone piers.
By 1835, it was considered that repairs would be to little avail and it became clear that a complete new structure was required. A new structure, that remains to this day, was designed by David Lennox, completed and opened in 1837.
 Illustration, James Jervis, The Cradle City of Australia: Parramatta 1788-1961, Sydney, Parramatta City Council, 1961, facing p. 202.
 Sydney Gazette, 22 Nov 1827.
 James Jervis. Cradle City, p. 116.