Windsor is the third-oldest European settlement in Australia, which is a remarkable claim for a pleasant, rather sleepy town of cafés and antique shops. Settlers began farming the rich Hawkesbury floodplain here in 1794, in an area first called Green Hills, and Governor Macquarie formally laid out the town in 1810. The Hawkesbury itself, brown and slow, bends past the old wharf, and the town has the habit of flooding, sometimes dramatically, which is why so many of the grander buildings sit on the rises.
Look for St Matthew's Church, designed by the convict architect Francis Greenway and finished in the 1820s, which has a plain, handsome look of the Georgian colony. Thompson Square, said to be the oldest public square in the country, still has early cottages around it, and the old Hawkesbury River bridge area keeps the flavour of a river town. With only about two thousand people in the core and bigger suburbs close by, you can find fuel and food easily, especially in South Windsor, a couple of kilometres away.
Riders know Windsor as the gate to the Putty Road, one of the great motorcycle roads of New South Wales. The route runs north for roughly 170 kilometres through the forest of Wollemi National Park to the Hunter Valley, with a long run of bends, rises and fast flowing sections, and rather little in the way of towns. It is a road of rhythm, not frills, with very few places to buy anything on the way, so fill the tank here and carry water. Be aware that speed limits are strictly policed, with fixed and mobile cameras and a regular police presence on weekends, and the road has a long record of serious crashes, so keep it honest.
The landscape beyond Colo is classic Australian bush: sandstone ridges, grey-green eucalypt, birds calling in the heat, and the sharp smell of leaf litter after rain. In winter, shade patches can hold cold air, and in summer the heat is ferocious by midday. Early on a weekday the road is quiet, kangaroos and the odd goanna on the verge, and the first bends after Colo are the reward for dealing with the suburban fringe.