The development of transport in Sutherland Shire has a rich history, beginning with water as the primary mode of transportation. Farmers utilized ships to navigate the coast into Botany Bay and up the Georges and Woronora rivers, circumventing wharfage and customs dues at Port Jackson. The first public road, known today as the Old Illawarra Road, was constructed between 1842 and 1845 using convict labor, creating a route to the "Five Islands" (modern-day Wollongong). This road was later connected to a new southern line completed in 1864 at Engadine, which now forms a part of the Princes Highway, the main north-south thoroughfare through the Shire.

The arrival of the railway marked a significant turning point in the region’s transport landscape. In 1884, a railway line was extended from Hurstville to support the burgeoning Illawarra district, which led to the establishment of a shanty town on the heights of Como. By 1885, the Sutherland railway station was opened, named in honor of John Sutherland, a Minister of Works in the 1870s who championed the railway's construction.

During this period, most of the Sutherland Shire was accessible only via rough access tracks. A direct road was soon established between the railway station and Cronulla Beach, primarily serving families and fishing enthusiasts. This development was complemented by the inauguration of the Sutherland-Cronulla steam tram service in 1911, which not only boosted the popularity of the Cronulla beaches but also facilitated the growth of local businesses in the area.

However, the rise of motor traffic led to a decline in tram passengers, resulting in the closure of the passenger service in 1931 and the cessation of the goods service the following year. To accommodate the increasing road traffic, the first road bridge into the Shire was constructed at Tom Ugly's Point in 1929. This was followed by the opening of the Captain Cook Bridge in 1965, a six-lane structure that replaced the inadequate ferry service, further enhancing access across the Georges River.

Today, Sutherland Shire stands as a testament to the evolution of transport, illustrating how advancements in infrastructure have shaped the region’s connectivity and development over the decades.