Windsor is a picturesque meeting place and the gateway to the Hawkesbury. Settled in 1791, it is the third-oldest place of British settlement on the Australian mainland. A feature is Thompson Square, the oldest public square in Australia surrounded by Georgian buildings including the Macquarie Arms Hotel (1794). There is a mall lined with historic buildings, a regional museum and regional gallery, and a township offering eclectic stores and cafés as well as several markets. Visit historic St Matthews Anglican Church (1817), designed by the famous ex-convict Colonial Architect Francis Greenway, - 'The Cathedral of the Hawkesbury'. It remains an enduring aesthetic and architectural statement within the Hawkesbury. The graveyard is one of the first three in the country ordered by Macquarie in 1810, making it older than the church. There are First Fleeter burials and famous Australians like John Tebbutt (astronomer) and William Cox (explorer, first road builder over the Blue Mountains, 1815), making a visit here stimulating.

Slow the pace right down and bring a picnic, (electric barbecues are available for public use) or meander along the riverbank on the Great River Walk from Windsor Bridge to Deerubbin Park, listening to birdsong. It is also a great place to walk the dog (in November the jacarandas are glorious). Additionally, there is now a public viewing platform that overhangs the river on the Great River Walk enabling superior views of the river, mountains and surrounds. There is a non motorised boat launching ramp in Macquarie Park suitable for kayaks and canoes. Windsor Canoe Club is ideally located in Macquarie Park. Walkers and picnickers are encouraged to visit Governor Phillip Park too with its riverside path, shelters, tables, electric barbecues, toilets and ample parking and grassed areas. This park now boasts a brand new water play area, fully fenced, for the kids. There is a public boat ramp in this park.

Grab your camera and try an evening shot from Windsor Bridge with the sun setting over the Blue Mountains and the river in the foreground. Windsor Cyclists welcomes new members - regular riding days in the Hawkesbury.

Visit the What's On page for information on market dates and enjoying historic Windsor. Windsor marks the end of the twice yearly Bridge to Bridge boat races: once with skiers and the other with fast boats alone. It's an exciting race that draws the crowds from Brooklyn in the east, as its starting point, to the finishing line in Governor Phillip Park, Windsor. October sees the annual Canoe Classic set off down the river from Macquarie Park, Windsor and into the night with an assortment of water craft with rowers and paddlers galore. There are many vantage points in Windsor to watch this colourful and animated flotilla set off.

Windsor has a railway station, which is part of the metropolitan system, and this suits walking groups that want to explore heritage-laden Windsor town without the hassle of driving. Also available are self-guided walking tour brochures to benefit such outings. They can be picked up from the Hawkesbury Visitor Information Centre and Windsor Regional Museum or online.

On the outskirts of Windsor the Hawkesbury Race Club is located at nearby Clarendon and horse race meetings are always fun here. There is a railway station at Clarendon for those without cars or those preferring not to drive.  Nearby is the Hawkesbury Showground home to many events throughout the year.

Windsor Country Golf Club is located in historic Windsor. It is an 18 hole Championship Course. The clubhouse enjoys panoramic views of the Blue Mountains.