Discover Historic Windsor

Nestled on the banks of the Hawkesbury River just 60km northwest of Sydney, historic Windsor is a popular day trip destination from anywhere in Sydney, for its historic charm, natural assets and many contemporary dining venues.

The town was first settled in the 1790s, making it the third-oldest British settlement in Australia. In the early 1800s it was developed under the guidance of Governor Lachlan Macquarie, who changed its name from Green Hills to Windsor after England’s riverside town, Windsor-on-the-Thames.

Today, you can still explore the convict trail, which remains relatively unchanged since first used and visit Windsor’s heritage buildings, many of which are well-preserved and still used for their original purpose.


Walk the Windsor Convict Trail; image by James Pipino via Destination NSW

A little history

The town of Windsor was established to grow food for colonial Sydney and it soon became known as the ‘the bread basket’. Its location on the flood plains of the Hawkesbury River was chosen for its rich fertile soils for agriculture and for its ship access.

Windsor was the first of five towns Governor Macquarie established in the Hawkesbury region during the mid to late 19th century; the others are Richmond, Wilberforce, Pitt Town and Castlereagh. The area has battled many floods, including the destructive Great Flood of 1867 which washed debris from Windsor to as far away as Barrenjoey Head on Broken Bay, almost 70km east.

Things to do in Windsor

Take a heritage walk

Many of Windsor’s original buildings still serving the community, including St Matthews Anglican Church and the courthouse, which were both designed by the convict architect Sir Francis Greenway.  These and other historic landmarks can be viewed by simply strolling the town’s streets and some, including the courthouse, have public access.

The most prominent historic buildings and sites include:

Windsor Square in McQuade Park, the site of the first stage of Windsor’s development.

St Matthews Anglican Church (1817), near the corner of Moses Street and Greenway Crescent, was commissioned by Governor Macquarie and designed by Sir Francis Greenway. The town’s inhabitants took refuge in the church from the Great Flood in 1867. Take a stroll through the graveyard, which predates the church. Many headstones of the town’s founders, First Fleeters and convicts feature bronze plaques.

The other St Matthews, the St Matthews Catholic Church on the corner of Tebbutt and Little Church street, wasbuilt in 1821.

The Convict Barracks on Macquarie Street were built in 1820 for the town’s convict gangs. In 1846 the barracks became the Hawkesbury Benevolent Society’s facility for the poor, aged and infirm. The Hawkesbury City Council owns the site today.

Thompson Square, named after Andrew Thompson who arrived in Australia a convict and became a wealthy entrepreneur, town magistrate and a close friend of Governor Lachlan Macquarie.

There are many historical buildings on the square including The Macquarie Arms Hotel, which was built in 1815, making it the oldest hotel building in Australia (look for the horseshoe on its outside wall, which marks the peak level of the 1867 Great Flood); and the Doctor’s House, built 1830.

The Courthouse on Court Street was also designed by Sir Francis Greenway in 1822 and is still an operational courthouse. You can enter the building when court is not in session. Across the street is the original inn where the first magistrates spent the night before court trials.

Tebbutt’s Observatory and House (1844) on Palmer Street, which was built by astronomer John Tebbutt who discovered the Great Comet of 1861.

The Toll House (1835) on Bridge Street.

 Windsor Railway Station (1864) and Public School on George Street.

You’ll find a detailed map of these buildings’ locations here.

Learn about colonial life

The town’s library and museum offer interesting insights into life in Windsor, past and present.        

You can visit the Hawkesbury Central Library and gallery at the Deerubbin Centre between George and Macquarie Streets any day of the week. Its Local Studies Collection has information on local and family history, while the gallery exhibits traditional and contemporary works by local artists.

Towards the river, the Hawkesbury Regional Museum at 8 Baker Street is the modern home of the remains of the Macquarie Wall, once part of the Macquarie Arms Hotel, as well as Georgian Howe House, local astronomer John Tebbutt’s celestial globe, a diary belonging to a member of the HMAS Hawkesbury recording the Japanese surrender during World War II, the unique Hawkesbury creation, the local and infamous Flabbit (flying rabbit), and more. It is also open seven days a week.


Picnic at the Hawkesbury River

A visit to Windsor isn’t complete without a stroll beside the Hawkesbury River, once home to the Dharug Aboriginal people, who caught fish and yams along its banks.

Riverside Governor Phillip Park is the perfect spot for a picnic with tables, shelters, electric barbecues, children’s playground and restrooms.

The wooden pilings on the north side of the river, near the Windsor Bridge are remnants of the old Windsor Wharf where convicts were brought ashore.


The Hawkesbury River is one of Windsor’s natural attractions; image by Paul Blackmore via Destination NSW

Arts, crafts and local delights

If you’re in town on a Sunday, enjoy a wander around the Windsor Crafts & Product Markets in Windsor Mall on George Street where local artists show their works and locals sell home-grown and homemade produce.



Shop for antiques at Windsor; image by James Pipino via Destination NSW

Visit Freeman’s Reach and Wilberforce

A 7km drive from Windsor, at Freeman’s Reach, is Reibycroft, a Georgian farmhouse the emancipated convict turned successful businesswoman, Mary Reiby built for her daughter in 1825. Like Andrew Thompson, Reiby became a respected and successful business owner who was one of the founders of the Bank of New South Wales (now Westpac) and who features on the Australian $20 note. It is a private residence but can be viewed from Gorricks Lane, next to the grain silo.

About 6km north is Wilberforce, which was also established by Governor Lachlan Macquarie and is known locally as Macquarie Town. It also has many historic buildings, including Macquarie Schoolhouse (1819) and St John’s Church (1879), the Wilberforce Cemetery (1815) and the heritage-listed Australiana Pioneer Village on Rose Street.

The Australiana Pioneer Village here is open every Sunday and features historic buildings, including a blacksmiths, a Bank of Australia, police station, and inn, as well as experiences to give you a taste of colonial life including blacksmithing demonstrations, a damper camp serving fresh hot damper with billy tea, a whip maker, sulky rides, and from March to June, Ghost Tours every Friday night.


Eateries at Windsor

Dining at Windsor provides enough reason to visit in itself, as the restaurant scene is competitive and diverse. The town provides the full range of meal styles, from fish and chips or pizza and pasta at bistros within historic pubs, to gourmet cuisine. On any weekend, you will also be tempted by all-day breakfast, high tea or gelato.

Plan your trip using this comprehensive guide to Windsor’s many charms, for a memorable visit.