The Southern Highlands has a rich history which began with the traditional owners of the land, the Gundungurra and Dharawal people.

The district was first explored by Europeans as early as 1798 when a party led by an ex-convict, by the name of John Wilson, made its way south on two occasions. Access to the area was forbidden by Governor King from 1805 until 1821, primarily to protect the government herds at Cow Pastures (now Camden), although the prohibition was frequently ignored. One of the most prominent of these interlopers was the Surveyor-General, John Oxley, who established a herd of cattle at a place named Argyle (now Moss Vale) in 1815. He had a bough and bark homestead built for himself, although he never occupied it, which he named ‘Wingecarribee’, from the Aboriginal words Wingie Wingie Charibee, meaning ‘waters to rest beside’.

Viticulture is not new to the area. With the establishment of the Australian Kerosene Oil and Mineral Company (1870–1911) at Joadja Creek, over 6 700 fruit trees and a table grape vineyard were planted providing the local area with fruit (including grapes) and supplying the Sydney markets with approximately one quarter of its needs.

Growing wine grapes originally commenced prior to the second world war but lapsed when the market was found to be non-viable. Recently, however, a re-awakening of interest in growing premium cool climate grapes  for the production of premium wines has led to the establishment of approximately 60 new vineyards and 16 cellar doors to visit in the area.