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The Southern Highlands’ main town began life in the 1860s when John Oxley, an early Colonial explorer, subdivided his land grant and a small township emerged. Home to an increasing number of urban refugees, Bowral has an arty, old-world feel, making it a popular and relaxing weekend destination for Sydneysiders. It is probably best known as the former home of the famous cricketer Sir Donald Bradman (see Sydney Cricket Ground).

Built by John and Elizabeth Macarthur (see John & Elizabeth Macarthur), this 1793 estate was once an important social, political and cultural centre. The farm’s cottage is the oldest surviving building in Australia, and is carefully furnished with reproductions of the original interiors.

Emancipated convicts James and Elizabeth Ruse established Australia’s first self-sufficient farm in 1789. In the colony’s first land grant, Governer Phillip gave them a further 12 ha (30 acres) for their efforts. The charming Colonial bungalow was built in the 1830s by the farm’s next owner, the surgeon John Harris.

Close by Elizabeth Farm, this cottage was named after a village in Hampshire, England. The Macarthurs built this cottage in 1824 as a retirement home for their governess, Penelope Lucas. The furnishings of the rendered sandstone cottage reflect the 1820s to the 1850s.

Overlooking the Parramatta River, this distinguished plastered brick residence (see Old Government House) is located on 105 ha (260 acres) of parkland. Australia’s oldest public building, it was built by Governors Hunter and Macquarie between 1799 and 1818. The porch is credited to Francis Greenway. The interior faithfully reflects the Macquaries’ era and their tastes, and houses one of Australia’s finest collections of 19th-century furniture. Tours explore the people who lived here as well as the eras they lived in.

The highlight of this quaint historical village is the charming Settlers Arms Inn. Built by convict labour between 1836 and 1848, this National Trust-classified pub overlooks the Macdonald River and offers good food and accommodation.

Governor Macquarie established five towns in 1810 on the fertile land around the upper Hawkesbury River, one of which was Windsor, now a weekend tourist haven. The town’s wonderful Colonial buildings include one of Australia’s oldest pubs, the 1815 Macquarie Arms Hotel, as well as the 1823 St Mathew’s Anglican Church and Rectory, designed by Francis Greenway (see Francis Greenway: Convict Architect).