The Wingecarribee River rises on the heights at Robertson, fictional home of Babe the pig. It flows westwards, away from the sea, across the Southern Highlands plateau, near Bowral and Moss Vale, to Berrima. Beyond this, the river enters a deep canyon and combines with the Wollondilly River in Lake Burragorang, a water storage created by Warragamba Dam.
It also runs through a valley on the plateau that is home to a popular camp, Biloela.
In its upper reaches, the Wingecarribee River forms the Wingecarribee Swamp, the only substantial peat bog in New South Wales. Most of the swamp has been drained and the remaining section of the swamp is the habitat of a number of endangered species.
The Shoalhaven Scheme pumps water from the Shoalhaven River into a reservoir created by a dam on the Wingecarribee River. This water supply augments the water supply for Sydney.