Sydney’s early penal settlement soon ran out of food as the shores around Botany Bay were too sandy to support agriculture. In 1789 Captain Arthur Phillip sailed north to Broken Bay and sighted the mouth of a river which Phillip named the Hawkesbury River after Lord Hawkesbury. He travelled to the area which had taken on the name ‘Green Hills” (now known as Windsor), where he noted arable land ideal for growing fruit and vegetables, and for grazing livestock.

By 1794, 22 families were farming the area, with more constantly arriving. At that time, much of the transportation was by river. When Governor Lachlan Macquarie arrived in Sydney in 1810, part of his brief was to prevent further losses of food stores, buildings and possessions caused by floods which had plagued the Hawkesbury since 1794. Macquarie gave these instructions high priority and established townships on the high ground in various parts of the district. Today many fine buildings from the 19th Century still survive providing insight into early European colonisation.

By 1794, settlers had moved into the area west of this town originally known as Lower Hawkesbury or Lower Portland Head. Grain and other crops were being grown for the colony by these early farmers who provided Sydney Town with almost half its food supply. The produce was delivered by boat down the Hawkesbury River, leading to the town rapidly developing as an important river port. This was the beginning of a riverboat industry, which continued throughout the 19th century.

By the 1830s the town was known as Wiseman’s as a tribute to Solomon Wiseman, the emancipated convict who operated the ferry service across the Hawkesbury River.

In 1825 the NSW Government began work on an inland road to connect Sydney to the Hunter Valley, a distance of 264 kilometres. Up to 720 convicts worked on the Great North Road and built stonework including buttresses, culverts, bridges and 9-metre-high retaining walls. The road was completed in 1836.

The Great North Road was not popular. It was isolated, had no permanent watercourses, and bypassed existing settlements. Coastal steamers became the preferred means of travel to the Hunter Valley, and by the time the road was completed in 1836 it was almost redundant.

The Old Great North Road is a 43-kilometre section that runs from Wisemans Ferry in the south to Mount Manning (near Bucketty) in the north. It runs within and adjacent to Dharug National Park and passes in and out of Yengo National Park.

It is called the Old Great North Road because it is the most intact section of the original road that remains undeveloped. The World Heritage-listed section of the Old Great North Road is about 7 kilometres long and lies within Dharug National Park. The road is closed to motor vehicles but can be walked.