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Wingecarribee Shire is the local government area of the Southern Highlands in the state of New South Wales, Australia. The Wingecarribee Shire is around 110 kilometres (70 mi) southwest of Sydney and is part of regional Capital Country and to some extent can be considered part of the Southern Tablelands. Wingecarribee Shire covers an area of 2,700 square kilometres (1,000 sq mi) that is typically referred to as the Southern Highlands. Wingecarribee Shire is an important catchment area for water supply to Sydney, Wollongong and the Northern Shoalhaven. The Council seat and Chambers is in Moss Vale. However, the centre of commerce of the Shire is in Bowral. The Shire came into existence on 1 January 1981 as an amalgamation of the three previous local government areas that made up the Southern Highlands; Mittagong Shire (itself an amalgamation of Nattai Shire and Mittagong Municipality), Bowral Municipality and the former Wingecarribee Shire (based in Moss Vale). In 2012, the Wingecarribee Shire Council won a landmark class action against Lehman Brothers Australia in the Federal Court after it was found that Lehman Brothers failed to give sound financial advice to the Wingecarribee Shire and other councils through exposure to high-risk investments known as collateralised debt obligations. Wingecarribee Council suffered A$1.5 million of losses on its investments. The Federal Court found that the council was entitled to an initial award of A$9 million. In 2016 Council announced they had recovered $9.5 million of the $11 million in total losses, recovering 85.6% of all losses. Council's total legal costs of $724,894 were also recovered. Before the council was suspended in 2021 and an administrator was appointed, the mayor of Wingecarribee Shire was Duncan Gair. On 20 May 2021, Lisa Miscamble was appointed General Manager.

The Southern Highlands, also locally referred to as the Highlands, is a geographical region and district in New South Wales, Australia and is 110 km south-west of Sydney. The region comprises the local government area of the Wingecarribee Shire and also towns of the Mulwaree Shire. The region is considered a wine region. The region specifically is the area centred on the commercial towns of Mittagong, Bowral, Moss Vale, Bundanoon and Robertson as well as the historic town of Berrima. Smaller villages like Burradoo, Sutton Forest, Colo Vale, Avoca, Yerrinbool, Exeter, Welby and many more that make up the Wingecarribee Shire are spread in between and around these main centres and serve mostly as residential areas. The Highlands geographically sits between 500 m and 900 m above sea level on the Great Dividing Range. Like other regions along this plateau such as the Blue Mountains to the north and the Australian Alps to the south, the Southern Highlands is known for its cool temperate climate. The Southern Highlands Shale Forest and Woodland and Blue Mountains and Southern Highlands Basalt Forests vegetation communities lie primarily within the region. The Southern Highlands as a region is part of the larger Capital Country Region with the Highlands forming the northern part of the region and the Southern Tablelands forming the southern part of the region.

Mount Gibraltar (Ngunnawal–Gundungurra language: Bowrell) is a mountain with an elevation of 863 metres (2,831 ft) AHD that is located in the Southern Highlands region, between Bowral and Mittagong, in New South Wales, Australia. Further west is Berrima.

Mount Gibraltar Trachyte Quarries Complex, also known as the Bowral quarries and The Gib is a heritage-listed former stone quarry on Mount Gibraltar at Oxley Drive, Bowral, Wingecarribee Shire, New South Wales, Australia. It was worked from 1886 to 1986, providing stone blocks from the igneous rock (both trachyte and syenite) for significant public buildings, monuments, and other uses, both locally and further afield, including overseas. The complex was listed on the New South Wales State Heritage Register on 2 December 2013.

Bowral railway station is a heritage-listed railway station located on the Main Southern line in New South Wales, Australia. It serves the town of Bowral in the Southern Highlands region of New South Wales opening on 1 March 1867.

Bowral ( BOW-rəl) is the largest town in the Southern Highlands of New South Wales, Australia. It is 132 kilometres (82 mi) south-west of Sydney and 169 kilometres (105 mi) north-east of Canberra. It is the main business and entertainment precinct of the Wingecarribee Shire and the Southern Highlands. Bowral once served as a rural summer retreat for the gentry of Sydney, resulting in the establishment of a number of estates and manor houses in the district. Bowral is often associated with the cricketer Sir Donald Bradman. Bowral is close to several other historic towns, being 5 kilometres (3 mi) from Mittagong, 9 kilometres (6 mi) from both Moss Vale and Berrima. The suburb of East Bowral and the village of Burradoo are nearby.

The New Empire Cinema is a cinema in Bowral, New South Wales. Also known as the Empire Theatre, and Empire Pictures, and open since 1915, it is the oldest continuously running cinema in mainland Australia. At times over the years, the title has defaulted to New Empire and there have been similarly named establishments in other Australian states. The New Empire currently has four screens, and can hold up to 560 people. The cinema is run by Richard Ruhfus, David Graham and Gerard Aiken, and a staff of 24 employees.

Capital Country is one of the sixteen tourism regions of New South Wales, Australia. It encompasses the Southern Highlands and the Southern Tablelands, including the Canberra District wine region, and borders the Monaro which surrounds the southern half of Canberra. It also sits roughly on the traditional lands of the Ngunnawal and Gandangara Peoples. The Capital area is one of the oldest agrarian areas of NSW and is a commuter region of Canberra, the nation's capital, and is to the southwest of Sydney via the Main Southern railway line and Bombala railway line. The towns and villages in Capital Country range from sophisticated to quaint; their surrounding areas are mostly rural. Capital Country is known for historical venues, antiques stores, and established open gardens. The major cities include Canberra, Queanbeyan, and Goulburn. Towns include: Bowral Braidwood Bundanoon Bungendore Crookwell Gundaroo Gunning Hall Mittagong Murrumbateman Marulan Tarago Yass Young Some permanent attractions and events in Capital Country are: International Cricket Hall of Fame in Bowral Brigadoon in Bundanoon Bungendore Village Square Garden Ramble, Bundanoon Kennerton Green one of Australia's most famous gardens, in Mittagong. Trail Ride, Tallong

Bradman Oval is a heritage-listed cricket ground in Glebe Street, Bowral in the southern highlands area of New South Wales, Australia. It was named after cricketer Don Bradman, who lived locally and played at the ground in the 1920s. His ashes are scattered on and near the Oval. It is also known as Glebe Park. It was added to the New South Wales State Heritage Register on 23 June 2000. It is an attractive ground, with a white picket fence and an old fashioned pavilion. The Camden Woollybutt is the main gum tree species surrounding the playing surface. It has a seating capacity of up to 5,000 people (using temporary stands). Bradman Oval and the nearby International Cricket Hall of Fame (which incorporates the Bradman Museum that operated 1989–2010) are tourist attractions for cricket fans in Australia, and for people visiting from overseas.

The Bradman Museum & International Cricket Hall of Fame is a permanent cultural exhibition dedicated to the game of cricket and Australian cricketing hero Sir Donald Bradman. The Museum located in the Australian town of Bowral, New South Wales. The exhibition opened in November 2010 in buildings formerly used by the Bradman Museum, which was devoted to the cricketing career of the Australian batsman Sir Donald Bradman. The Bradman Museum opened in 1989. The Hall of Fame incorporated all of the former Bradman Museum's holdings. The Bradman Museum was, and in effect remains, the only museum in Australia dedicated principally to an individual. The International Cricket Hall of Fame is adjacent to Bradman Oval, which was named after Sir Donald Bradman in 1947. The Oval was where he played many games in his early years, and where his and his wife's ashes are now scattered. The oval and museum are significant tourist attractions for Australians with an interest in the legend of Sir Donald Bradman, cricket fans in Australia, and for many people visiting from overseas. In 2016, after the ODI win over India in Manuka Oval, Canberra, on their way to Sydney Cricket Ground, the squad became the first Australian squad to ever visit the Museum.

Bowral and District Hospital is a community hospital is servicing the Southern Highlands region in New South Wales, Australia. The hospital is centrally located in the town of Bowral and is the only hospital operated outside the Sydney metropolitan area by the South Western Sydney Local Health District.

Bowral High School is a government-funded co-educational comprehensive secondary day school, located in Bowral, a town in the Southern Highlands region of New South Wales, Australia. Established in 1930 as a tribute to the Australian and New Zealand Army Corps (ANZAC) of World War I, the school caters for approximately 850 students from Year 7 to Year 12, of whom five percent identified as Indigenous Australians and twelve percent were from a language background other than English. The school district includes Bowral, East Bowral, Mittagong, Colo Vale, and Hill Top. The school is operated by the New South Wales Department of Education; and the current principal is Richard Finter.