Being the third settlement in the colony of New South Wales, The Upper Hawkesbury is full of history and heritage, and as such is an ideal place to visit for those who have an interest in the early days of our nation. During its first 100 years, the colony relied on the Uppper Hawkesbury River for its food. Today, it is steeped in history, with sleepy colonial era villages, Aboriginal habitation sites and convict relics awaiting discovery.

Length: 200 km return (from Sydney CBD)

Minimum duration (one way): 1 day in each direction

The drive commences at Windsor, a river town established in 1794 to produce the crops needed to avert a famine at Port Jackson (Sydney). The first settlement on the Hawkesbury, it became a bustling port. Many buildings from its earliest years remain.

From Windsor, the drive follows the northern bank of the Hawkesbury in an easterly direction. Before leaving Windsor, we recommend the short drive to Pitt Town on the southern bank of the river. Pitt Town is a 'Macquarie Town', a collective name for five towns established on the Hawkesbury River by Governor Macquarie in 1810. It developed slowly and is today still a sleepy village. Beyond pitt Town is Cattai National Park. Originally occupied by the Dharug people, the has aboriginal axe grinding sites, rock engravings and Aboriginal art sites. Ther park the site of a land grant to the First Fleet assistant surgeon, Thomas Arndell. Arndell's cottage, dating from 1821, is still in the park

Return to Windsor, cross the river at Bridge street and head north to Wilberforce, another Macquarie Town. Wilberforce currently boasts Rose Cottage; the oldest timber slab cottage in Australia standing on its original site along a recreation of the pioneer village. Nearby is the butterfly farm, Indy 800 kart track and ski garden. Waterskiing in Australia was pioneered on the section of river between Wilberforce and Sackville, and is still Sydney's primary water skiing location.

Between Laughtondale and Windsor, there are a number of reaches named in the early 19th century after the dukes who were the sons of William the fourth: Gloucester, Sussex, Cambridge, Cumberland, Kent and Sackville. At the time, it was customary to name geographical features in new settlements after important people in England in the hope that they would do something for you in return. NSW Gov. Lachlan Macquarie had the practice down to a fine art, and used these same names with gay abandon in other localities around NSW, including the streets of Sydney, so he is likely to have been the culprit here.


Take King Road (which later becomes Sackville Road) to Ebenezer, the site of Australia's oldest church (1809). It has been beatufully restored, and devonshire teas (highly recommended) are served from the old schoolmaster's cottage nearby. The cottage houses a small museum of photos and furniture, with records of the pioneer settlers. Well worth a visit.

Head back to Tizzana Road and turn right, following it past the historic Tizzana Winery (1887) and through the village of Sackville which straggles along the road beside Sackville Reach. Watch out for the old cemetery on the right where two first fleeters are buried. Sackville Ski Gardens, with its caravan park, wharf and boat ramp, is where water skiing on the Hawkesbury first began in the 1950s.

At the end of Tizzana Road, turn left (rather than take the ferry) then immediately right, and follow West Portland Road to Lower Portland. As you approach the Colo River bridge, turn right towards the Lower Portland ferry. Take the ferry across the river, turning left into River Road. The road to Wisemans Ferry is quite narrow and twisty with some blind corners, so take extra care, but be rewarded by the delightful river views.


As you approach Wisemans Ferry, take the Webbs Creek ferry back across the Hawkesbury and follow the road to St Albans. This road travels through Lower Macdonald up the Macdonald Valley on the river's western bank. The 21 km drive through the narrow valley to St Albans is extremely picturesque. Take the bridge across the river at St Albans. You have now joined the original road from Sydney to the Hunter Valley, pioneered and built by convict road gangs in the 1820s.