<p>This dissertation examines why it was important to build a quay in Sydney Cove between 1839 and 1855 despite recurring market and financial distress, the topographical difficulties of the site and the technological constraints of the times. The history of construction of a masonry quay at the head of the cove, and a timber wharf on the cove’s western shore — collectively known as ‘Circular Quay’ — has received only limited research attention since its completion in the mid-nineteenth century. Yet, building the eastern masonry quay was a major engineering work, which involved extensive quarrying on the interface of the cove itself, and the reclamation of tidal flats and marshland at its head. There were urgent incentives for the replacement of the primitive and decaying public wharves in the cove. The new quay had to complement the viable competitive environment that grew out of the colony’s advancement from a penal settlement to a “free” society. Therefore, in writing the narrative of the Quay, attention is paid to the development of trade in the colony and the search for a reliable and sustainable staple to support it economically. Authorising, influencing, and sometimes obstructing the construction of both the masonry quay and the timber wharf, was an often restive and troublesome Legislative Council. The political manoeuvrings of its members around the inclusion of elected representatives in 1843, and at the approach of responsible government in 1856, meant that ‘Quay questions’ were raised during the construction of firstly the masonry quay, and then the western timber wharf, which consequently fed into the general murk of condemnation, by political factions, of expenditure, contractors and government officials, and design quality. A year after the shoddily constructed western wharf was completed in 1855, it was sinking in parts, leaving the newly formed government undecided about what to do with a ramshackle timber structure that had cost far too much to construct.</p>