In 1957, Clinton Hartley Grattan, one of Australia’s most important foreign observers, wrote of the shadow of the “urban” in legends of the Australian “bush”.1 He argued that the early frontiers of Australian settlement were frontiers of men with private capital, or entrepreneurs, and those frontiers thus carried more elements of the urban than is commonly realised. Such early colonial enterprises around Australia’s south and southeastern coasts, and across the Tasman included sealing, whaling, milling and pastoralism, as well as missionary, trading and finance ventures. In advance of official settlements in the late-eighteenth and early-nineteenth centuries, entrepreneurs mapped coastlines, pioneered trade routes and colonised lands. Backed by private capital they established colonial infrastructural architecture effecting urban expansion in the Australian colonies, New Zealand and beyond. Yet this architecture is rarely a subject of architectural histories.