The Old Great North Road was constructed using convict labour between 1825 and 1836 as the first overland route between Sydney and Newcastle. In the two centuries since, much of original road has been rebuilt and paved while the country around it has been developed for agriculture or settlement. However, 47km of the original route, from near Wisemans Ferry on the Hawkesbury River in the south to Bucketty in the north, remains unpaved and almost entirely closed to motor vehicles.
This section starts at the gate at the bottom of historic Devines Hill and for the first few kilometres climbs through a World Heritage listed section in Dharug National Park with excellent examples of convict work until it reaches the Yengo plateau. From there it follows the Old Great North Road northwards through heavily forested Yengo National Park to the finish at the obelisk in the Bucketty Historic Road Precinct. The route passes atmospheric Ten Mile Hollow, where a convict stockade once existed, the sandstone pillars of Clares Bridge, the second oldest bridge in Australia, and the remains of Circuit Flat Bridge, along with many other preserved and restored remnants of the original road and its convict builders including timber and stone culverts, cut stone drains, sandstone-block retaining walls, convict graffiti and camps.
Despite a dearth of facilities, the remote Old Great North Road is popular with hikers, trail-runners and mountain-bikers, and the Terrigal Trotters running club has regularly organized social trail runs along sections of the route.
More information about the Old Great North Road can be found at https://www.environment.nsw.gov.au/topics/parks-reserves-and-protected-areas/types-of-protected-areas/world-heritage-listed-areas/australian-convict-sites-old-great-north-road, https://www.convicttrail.com.au/uploads/8/7/1/9/87196654/cartoscope_convicttrail_map.pdf and https://en.wikipedia.org/wiki/Great_North_Road_(New_South_Wales).