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The historic township of Windsor is located within the Hawkesbury local government area. Being the third-oldest colonial settlement in Australia, the old school charm of the town is clearly shown when talking a walk through the leafy streets. The traditional custodians of the Windsor area are the Darug People.


With a train station located at the southern end of the town, Windsor can be accessed by either train or car. If you choose to drive, we recommend parking towards the station side of town. It will allow you to walk throughout and experience all the History Windsor offers through the street architecture. Start your day by walking up George Street, taking in all the sights of the buildings surrounding the town. Be sure to look up and really take some time to appreciate the colonial architecture. Then, if you are in the mood for a coffee, continue up George Street to Cassiopeia Coffee, Windsor. You will know you’ve arrived once you see the coffee sign – literally!

Cassiopeia is a specialty coffee roaster based in the Blue Mountains and founded in 2006. Windsor is lucky to be one of them, with only four espresso bar locations. It is a must-visit whilst in town!

Continuing up George Street, the street will turn into a pedestrian mall for the next two blocks. The leafy thoroughfare was opened in 1984, providing a public space for both visitors and residents alike. Take note of the buildings lining the Mall, with many examples of nineteenth and early twentieth-century architecture. On Sundays, the Mall comes to life with market stalls and the like.

With laneways full of art, be sure to check out some of the side streets. Then, if your appetite is growing, head up to Crepe Escape on George Street. With a Parisian infused menu, opt to sit alfresco so you can enjoy the views of George Street while sipping on a wine with a crepe of your choice.

After filling up on Crepes, head over to Gelato 66 across the road, which craft a great selection of artisan gelato – there is sure to be a flavour to suit every taste. Gelato 66 provides a selection of fresh gelato as well as providing wholesaling of their goods to many stores within Windsor.

Head down Thompson Square and onto The Terrace, where you will find yourself walking along the Hawkesbury River.

Heading back up Baker Street, be sure to stop off at the Hawkesbury Regional Museum. The purpose-built museum showcases some of the most important artefacts of the third oldest settlement in mainland Australia. In addition, the museum showcases multiple exhibitions, where it is free to enter but a small fee charged for group tours.

If you are still in the mood for some culture, meander back through the streets of Windsor towards the Regional Art Gallery located at the Deerubbin Centre at 300 George Street. While walking to the gallery, take the backstreets this time rather than George Street. Be sure to look up to appreciate the pastiche of design styles and time periods.

Arriving at the Art Gallery, walk through the main doors up to the first floor of the building. The gallery showcases some of the finest travelling exhibitions, such as Safe Space, a major touring exhibition of contemporary sculpture, as well as Promiscuous Provenance by Anna Glynn. The gallery is also home to a permanent collection featuring works by artists such as Ben Quilty, Lloyd Rees, Arthur Boyd and Norman Lindsay, to only mention a few. The Gallery Store is also home to a range of products designed to complement the exhibitions, programs, and activities.

If time permits, take a drive across the Hawkesbury River onto Freemans Reach Road. The road follows the river and gives spectacular rural views of the turf and vegetable farms that reside in the area. These views showcase a vastly different side to Windsor and should be explored and appreciated.

With plenty to see and do throughout the town, you may be inclined to come for a weekend and spend the night. With an array of accommodation options available from guesthouses, Airbnb and hotels, you will be spoilt for choice. The Crowne Plaza is located five minutes out of town, and it set upon the Rum Corps Barracks Golf course. With a bar, restaurant, day spa, and immaculate gardens, you are sure to remember this stay.

For some late-night antics, Windsor has you covered. Back on George Street, be sure to check out Plan B Bar. A kitsch bar located upstairs, giving great views over George Street. With an extensive burger menu, as well as a list of custom cocktails and their own beer, Plan B is the perfect spot to unwind for a few drinks.

For a more quintessential Windsor experience, be sure to check out The Church Bar on Kable Street. Unlike anything else in Windsor, the Church Bar is situated within an original Church, built in 1869. Open for lunch through to dinner and drinks, visiting the church bar becomes an experience of itself!


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