The Old Great North Road is one of the most remarkable pieces of engineering in Australia, and it was built by men who had no choice. Between 1826 and 1836, convicts were set to work cutting a road from the colony at Sydney north to the Hunter Valley, a distance of well over two hundred kilometres, through some of the most broken sandstone country on the continent. They cut deep into the rock with hand tools, built retaining walls of carefully fitted stone, and carried out the work in chain gangs under harsh discipline. The most spectacular surviving section is Devine's Hill, a steep climb with tall dry-stone walls that still look perfect after almost two centuries.
The surviving parts of the road are UNESCO listed as part of the Australian Convict Sites, and the setting is a bushland of sandstone ridges, gum trees, tree ferns in the gullies, and the broad, slow Hawkesbury river in the valley below. At Wisemans Ferry, the road crosses the river by a free cable ferry that runs round the clock, and the crossing itself is a small event, with a short wait and a pleasant clunk of cables. Beyond it, narrow, winding tarmac and gravel climb into Dharug National Park, where you can walk sections of the original road, the walls overgrown with moss and lichen.
For a rider, the roads around here are a mix of twisting sealed sections and unsealed tracks. The surface is not always forgiving, with patched asphalt and loose gravel on the edges, and heavy rain can wash stones across the road. Weekends bring cyclists and cars out from Sydney, so go early in the morning for the quietest riding and the best light. Wildlife, from lyrebirds to wallabies, lives in the bush, and you will hear them as often as you see them.
Fuel is the main practical point. The district has few stations, and Wisemans Ferry has limited supplies, so fill the tank before you come. East Kurrajong, about twenty-three kilometres away, and Kariong on the coast side are the closest larger places. Winter is cool and clear, spring is good, and summer brings heat and the risk of bushfires, when roads can be closed with little warning. Check the fire warnings before you set off in hot weather.