One of the earliest colonial settlements of the Southern Highlands, the village of Windsor preserves its past with more than 20 colonial-era buildings, heritage walks, paddle wheelers and a charming Georgian town square. It’s also an enclave of Darug Aboriginal culture and regional art and home to renowned cycling and bushwalking trails.
Things to do in Windsor
Get oriented in Windsor with a stop by Hawkesbury Museum and Tourist Centre, which sits in the heart of Thompson Square. You’ll get a deep look at the Aboriginal culture and learn about European settlements throughout the centuries.
Pick up some maps and guides for the Windsor Heritage Walk, where you can admire 19th-century State Heritage Registered buildings along North Street and discover architectural feats by famous convict Sir Francis Greenway. Keep an eye out for The Windsor Courthouse and St. Matthew’s Anglican Church, considered a national treasure.
Travelling with the family? The kids will be thrilled with a ride on the Hawkesbury paddle wheeler, a re-created 1800s journey along the Hawkesbury River. Check the schedule for special cruises, such as the two-hour Sunday Music Cruise with a live band and barbecue lunch.
Back in town, discover local artists at the Hawkesbury Regional Gallery, then enjoy kayaking or canoeing at Governor Phillip Park. Meander along the region’s food and wine trails, including the Hawkesbury Harvest Farm Gate Trail, where you can meet growers, winemakers, artisans and chefs. In the evening, raise a glass in one of Australia’s oldest pubs, tucked inside the Macquarie Arms Hotel.
Windsor lies less than 60 kilometres north of Sydney, where you can take a train or bus or pick up a rental car at the airport. You can rent a bike in Windsor to explore the heritage, wine and food trails.