Welcome to Windsor

Windsor: a day exploring the Historic outskirts of Greater Sydney

A Self-Guided Walk in Windsor, Sydney

Download the Walking Map

I’m pretty excited about my excursion today. I am venturing to historic Windsor. Situated on the opposite end of the Hawkesbury River to where I live, it will take two hours to get there.

I have a good book to pass the time, but as houses give way to countryside, I drag myself away to appreciate the rural setting. Farm animals and rustic cottages dot the green fields. Vegetables growing in rows alongside the tracks, will one day grace tables in the city.

Sandstone houses

Stairs and sandstone

Historic Houses of Windsor

Ironwork detail

Heritage walking tracks

Windsor was the third area to be settled by the British after Sydney Cove and Parramatta. I have often thought about visiting this community on the North-western outskirts of Greater Sydney. Four Heritage Walks prepared by the Hawkesbury City Council have given me a plan. I’ll wander and enjoying the day out, more or less following their routes.

Alighting from the train, I make my way along George Street to Thompson Square. Passing the Railway hotel, I can’t help but notice four men in jeans and broad brimmed felt hats sitting in the hotel courtyard nursing a beer. It’s 9:30am.

The houses here are old. Many are weatherboard with brick chimneys projecting from often rusty corrugated iron roofs.

War memorial in Historic Windsor

War Memorial

Historic building in Windsor

No longer a Theatre

The early morning light reflects off the water as ducks splash in the pond at McQuade Park. A nearby memorial has is a surprising connection to the country of my birth. I recall stumbling across something similar in Parramatta. This obelisk is dedicated to soldiers from the area who lost their lives “in service to the empire in South Africa”. I carefully avoid the rotating sprinkler to read that a trooper died accidentally in the Vaal River in 1901 and another died from Enteric Fever a year later in Zeerust.

Breakfast calls, so I stop at the Lime and Coconut Café for coffee and a delicious haloumi and zucchini stack. The water ski decorating the wall reminds me that the annual Bridge to Bridge Ski race ends here in Windsor. It starts where I live on the Hawkesbury River.

Riverview Shopping Centre

On my way to the Riverview Shopping Centre (the nearest bathroom), the loud roar of an Airforce jet rushes over my head. The Richmond Air Base is close by.

Historic Windsor

More ironwork

Windsor Mall

As seen in Windsor Mall

Riverview Centre is like any other shopping mall. Sparkling, clean and lacking in character. Except for a bronze plaque to Governor Macquarie set in the marble-like floor. Then I notice that grey stripes placed in intervals on the floor are in fact a timeline starting with an acknowledgement of the original inhabitants of the land, the Dharug people.

I read that the area was first called Green Hills, that Napoleon allegedly planned to invade the Hawkesbury (which on further reading turns out to have had some substance) and when “the Terror of Windsor”, bushranger George Armstrong was captured. I walk through the mall to check if there really is a river view. River glimpses maybe.

Mill in Windsor Mall

Reminder of Mills of old

Community feel in Windsor

Waiting to be played

Windsor pedestrian mall

Wandering through the Windsor pedestrian mall, I look up at the old facades of the two storey buildings. Some are decorated and others indicate the year of their construction. Many date from the early to mid-1800s.

A man, rugged up but shivering from the cold, sits on the cold concrete with a sign asking for help. He tells me that a woman bought him a pie earlier but he wouldn’t say no to a coffee. Hopefully the flat white with three sugars that I buy him will warm him a little.

Thompson Square

I can’t find Thompson Square and wander towards the river past some elegant restored homes to the Hawkesbury Regional Museum. It is small and well set out with interesting local artefacts. An example of the mythical flabbit, a cross between a bird and a rabbit, is on display.

A miniature replica of the General Gordon Paddle steamer (another link to where I live as it plied the Hawkesbury River prior to the railway bridge being built) interests me. I read about the regular flooding of the Hawkesbury and the impact this has had on the district.

Anchor and Pioneer

Anchor and Pioneer

Protesting to preserve the history of Windsor


It turns out that Thompson Square is not the hard-surfaced area surrounded by shops that I was looking for, but the park that I walked past earlier. Convicts were called to work from the nearby Bell-post or whipped at the whipping post. An anchor is a reminder that boats transported much needed supplies from here to Sydney Cove.

A tent provides protection for protestors against the Windsor Bridge being replaced. I cross the controversial bridge and admire the large expansive Hawkesbury River.

Crossing the river at Historic Windsor

Controversial Bridge

Old Cottage in Windsor

Old Cottage

Windsor countryside

Having walked from one end of Windsor to the other along George Street, I find myself in the countryside. The air is crisp and fresh. There are horses in a paddock on my right and a man walking his dog on my left. A car pulls over. The older driver wants to spare me a walk. He tells me that my next stop (the John Tebbutt Observatory) is closed and is up for sale, but I can still photograph it from outside.

Having been in the family since the early 1800s, it really is the end of an era. Apparently besides discovering two comets, John Tebbutt produced a large body of scientific research.

Windsor Countryside


John Tebutt Observatory

John Tebutt Observatory

Australia’a oldest courthouse

Walking back past the oldest courthouse in Australia, I think it may also be the prettiest. Wooden benches provide comfortable seating in the newly mown grassed garden. A sign on the wall stating that “Aggressive or violent behaviour will not be tolerated.” contrasts with the peaceful setting.

The Tollhouse (re-erected in 1864 after collapsing due to floods), collected tolls until 1887. I walk under the road bridge. Someone has set up home here. A new looking baby stroller is parked on the edge of the footpath. I hope the child is not homeless too. I follow the path to the Greenhills burial grounds where early convicts are buried.

Windsor Seafood

Macquarie Arms Hotel

Macquarie Arms Hotel

Back in George Street, Windsor Seafood is busy despite mixed reviews. The homeless man in the mall has gone. I wander up and down Fitzgerald and Kable streets, spending time photographing the old water tower (built in 1889 and still in use today).

A woman sitting at a bus stop tells me that she prefers the Windsor Shopping precinct to the Riverview Centre which “has very little apart from Real Estate Agents”. She says that the tyres were stolen off their car while they were eating at a local restaurant, so now she prefers to use the bus.

Old advertisement on wall

Ghost sign

not much graffiti or street art in Windsor

The only Street Art I saw

I take an indirect route back to the station past the now privately owned “Bell Inn”. The veranda is beautifully decorated with white wicker chairs and bits and bobs. I’ve noticed that many churches of the churches in Windsor have been repurposed. One is a bar, another a Thai Restaurant. Some houses have maintained their heritage look, others have been modernised.

Windsor water tower

Water tower still working

North Street Cottage

North Street Cottage

Final thoughts on Windsor

I have had a good day. Without reading the extensive notes provided with the Heritage Walks, I have still managed to get a good feel of the place. I missed a walk along the river and other parkland.

And I really need to read more in depth about the buildings. Windsor deserves more than a day to explore. I think I’ll come back and overnight sometime soon.

The Bell Inn

The Bell Inn

Ironwork in Windsor Houses

More ironwork

Windsor has History. You’ll also find history in Kings Cross and Parramatta. Take a look.

Useful information:

Windsor on the western outskirts of Sydney is 46km north west of metropolitan Sydney .

Plan your trip at transportnsw.info

I combined a number of walking guides for my walk through Windsor. Here are a few:

Windsor Walking guide

Thompson Square precinct

The Peninsula precinct

The Mall Precinct

McQuade Park precinct

Walking Map

And a map to assist you: (You can download it here)
(NOTE that the time indicated on the map does not allow for any stops. I take an average of 4-5 hours when I explore):

Windsor walk map


    1. Author

      Thanks. I just have to work with the light as it is on the day I visit. Jo

  1. This looks like a great place to visit, the courthouse building is impressive and I love the detail of the ironwork.
    Who would have thought to find a monument dedicated to soldiers involved in the Boer war?

    1. Author

      I’ve noticed on my suburban walks that there are many Boer War memorials, Bernadette. They sometimes stand alone and other times are near a WW1 and/or WWII memorial.

  2. So glad you enjoyed your day in Windsor and thankyou for sharing.

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