Stand on the banks of the Hawkesbury River at the wharf west of Thompson Square and imagine the year is 1810. Governor Lachlan Macquarie has spent the last few days of December surveying the countryside and decided to name sites for new villages, and change this place, known as Green Hills, to Windsor. Macquarie established the village sites on high ground since the river has flooded regularly, sweeping away farmhouses, crops, animals and some residents to their death. These Macquarie towns were Wilberforce, Pitt Town, Castlereagh, Windsor and Richmond. Windsor became the premier town having river access to the sea, the only way farm produce could be conveyed to settlement in Sydney.

Governor Arthur Phillip had named the area Richmond Hill in 1789 and Windsor was the sister town upstream on the River Thames in Surrey, England.

Governor Arthur Phillip returned to England and Major Francis Grose was left in charge of the colony. He settled twenty two officers of the New South Wales Corps and some convicts who had completed their sentences on large parcels of land on the banks of the Hawkesbury in 1794. Boat building flourished enabling the farmers to ship vegetables easily to Sydney. Water-powered flour mills were also built to take advantage of the tidal flow of the river. The first mill to grind locally grown grain was built in the middle of the town in 1816. At one stage there were twenty six water-mills along the Hawkesbury-Nepean river system.

A road was built from Parramatta to Windsor to improve communications between settlements and Richard Rouse was commissioned to erect Toll Gates and collect a fee to pay for the road. The Toll House may still be seen in Windsor at the western end of South Creek Bridge.