The region is today recognised for its impressive 19th and 20th century buildings and streetscapes as well as for its natural and farming landscapes. European settlement commenced in the area around 1820.
Properties such as Throsby Park, Oldbury, Vine Lodge and Wingecarribbee have buildings dating back to the early to mid 19th Century which survive today.
The first settlement, Bong Bong settlement, located on the Moss Vale Road between Moss Vale and Burradoo adjoining the Wingecarribee River, is marked by an obelisk and sits within the greenbelt between Moss Vale and Burradoo as part of the Burradoo Landscape Conservation Area.
Berrima, the second settlement to be established in the district, dates back to the 1830s and survives today as the last remaining, largely intact, Georgian-period town on mainland Australia.
The 1860s saw rapid development through the advent of the Main Southern Railway Line. Mittagong, Bowral and Moss Vale grew quickly. A number of settlements across the Shire sprung up in the late 19th century and early 20th century including Bundanoon, Exeter and Burrawang. Joadja, located west of Mittagong, was a mining town of significance between the 1880s and 1920s. While significant parts of this State Heritage Listed and Nationally significant "ghost town" are still in existence, recent conservation work undertaken with the assistance of Council and a grant from the Federal Government has slowed and reversed the deterioration of its remaining buildings and structures.
The countryside has played an important part in the development of the area for farming as well as quarrying. Cooler climates, reliable rainfalls and good soils attracted many farmers who cleared a large part of the Shire’s remnant vegetation, resulting in today’s landscape mix of open paddocks and bushland areas.