North of Sydney, where the Hawkesbury River winds between sandstone cliffs and forested ridges, there is a road that convicts built by hand. The Old Great North Road, begun in the 1820s, was meant to link Sydney with the Hunter Valley, and it was cut and paved by gangs of prisoners working with picks, hammers and iron bars, often in chains. It runs for over two hundred kilometres, and several sections survive, with walls of fitted sandstone, culverts, drains and cuttings that still look neat after two centuries. Together with other sites it is part of the UNESCO-listed Australian Convict Sites, which record the transportation of about 160,000 men, women and children from Britain.
The best-known section is at Devine's Hill, near Wisemans Ferry, where a long retaining wall holds up the road on a steep slope. Walking along it, you see the marks of tools in the stone and feel the sheer labour. Other sections, such as Finch's Line or the Convict Trail, are quieter bush tracks. It is a sobering place, but also one with beauty, with eucalyptus forest, birdsong, and views down into the river gorge.
For a rider, the area has fantastic roads. The ride from Windsor or Dural up to Wisemans Ferry follows the river and the cliffs, and the free cable ferry at Wisemans Ferry crosses the Hawkesbury, which is a quirky little experience for a bike. The tarmac along the river is good, with long bends and some tight corners, and beyond lies the Putty Road, a favourite for motorcyclists, though it is policed with cameras and enforcement patrols. Spring and autumn are the best seasons. Summer can be hot, with bushfire risk and smoke, and weekends are busy with Sydney riders.
The listed nearest towns are small, so fuel should be taken in the larger places such as Windsor, Kariong or Dural before you go in, as stations in the valley are few. Wisemans Ferry has a pub and a few cafés for refreshments. Bring water if you walk the old road, and wear sturdy shoes, since sandstone can be slippery. Mobile coverage in the gorge is patchy, and a map is worth carrying. Tell someone where you plan to go if you walk beyond the main track.