Windsor is a portal to Sydney's past, as the third-oldest colonial settlement in the Australia it's brimming with colonial architecture. Explore the area's history on heritage walks and paddlewheeler river cruises. Its location in the beautiful Hawkesbury also makes it a great spot for outdoor adventures, from sailing to bushwalking.
Things to do
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 Walk.
It takes in Thompson Square, one of Australia’s finest examples of a Georgian town square. You also have 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 Valley Heritage Tours or the Hawkesbury Sightseeing Tours. As well as colonial heritage in the Hawkesbury Regional Museum you'll discover the rich indigenous cultural heritage of the local Darug Aboriginal people.
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. The Sydney Blues and Roots Festival in October is a big drawcard.
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 or hire a kayak from Hawkesbury Kayaks. You can also go fishing, waterskiing and wakeboarding on the river.
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.
Harvest Farm Gate Trail showcases the area's best produce, including gourmet goat’s cheese and native ingredients. Have lunch at The Cooks Shed, which is all about local produce. There are also three vineyards dotted along the Hawkesbury which offer tastings at their cellar doors.
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 for a memorable stay, or if you get seasick there's the waterside Crowne Plaza Hawkesbury Valley.