Windsor is a portal to Sydney's past. Settled in 1791, it's the third-oldest place of British settlement on the Australian mainland, and brimming with colonial architecture. Discover the area's rich history on heritage walks and paddlewheeler river cruises, before enjoying its old-style pub, quaint wineries and local foodie trail. Its location in the beautiful Hawkesbury also makes it a great spot for outdoor adventures.



History & heritage

Windsor offers a unique insight into Australia's past. There are 21 colonial buildings still standing  discover the story behind them and learn about the important role the town played in the fledgling colony with the self-guided Windsor Heritage WalkIt takes in Thompson Square, one of Australia’s finest examples of a Georgian town square, as well as St Matthew’s Anglican Church and the Windsor Court House, both designed by the famous colonial architect Francis Greenway, who arrived in the colony in 1814 as a convict.

If you prefer to have a guide show you the way and entertain you with anecdotes, join Hawkesbury Sightseeing Tours. As well as delving into the town's colonial heritage at the Hawkesbury Regional Museum (which you can also visit outside of a guided tour if you are short on time), you'll learn about the rich Indigenous cultural history of the local Darug Aboriginal people.

The heritage-listed former residence of 5 Thompson Square, Windsor

Thompson Square, Windsor

Things to do

Windsor boasts a vibrant arts scene. The Hawkesbury Regional Gallery has captivating exhibitions and a wonderful collection, including works by famous artists such as Arthur Boyd, Norman Lindsay and Ben Quilty, as well as an on-site library and cafe. The Sydney Blues and Roots Festival in October is a big drawcard to the area.

Set on the banks of the Hawkesbury River, you're spoilt for choice when it comes to outdoor activities. If you don't like the sound of motors, hop on the Hawkesbury Paddlewheeler (please note: cruises are currently on hold due to damage to the area's wharves during the recent floods) or hire a kayak from Hawkesbury River Kayaks. You can also go fishing, waterskiing and wakeboarding on the river. For something slower-paced, meander along the riverbank on the Great River Walk in town.

Eat & drink

Windsor is home to one of Australia’s oldest pubs, the Macquarie Arms Hotel. Built in 1815, on orders from then-Governor Lachlan Macquarie, it's the oldest building in Thompson Square, named after wealthy emancipist Andrew Thompson, a policeman, farmer and businessman.

The Harvest Farm Gate Trail showcases the area's best produce, including gourmet goat’s cheese, local wines, hand-picked fruits and native ingredients. There are also three vineyards dotted along the Hawkesbury which offer tastings at their cellar doors Bull Ridge Estate Wines, Jubilee Vineyard Estate and Tizzana Winery. If craft beer is more to your taste, head to the nearby town of Richmond, just a 15-minute drive by car, to Gypsy Fox Brewing Co, open to visitors on Saturdays and Sundays.

Jubilee Vineyard Estate, The Hawkesbury

Jubilee Vineyard Estate, The Hawkesbury

Getting there

Windsor may feel like it's a world away from the cosmopolitan buzz of the CBD, yet it's only 50 minutes’ drive northwest of the Sydney Harbour Bridge. Accommodation options range from houseboats to river cabins, or if you get seasick there's the waterside Crowne Plaza Hawkesbury Valley.


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