The residential suburb of Castlecrag overlooks Middle Harbour, in Sydney's North Shore. The original inhabitants of the region were the Camaraigal people, who referred to the entire lower north shore as Cam-mer-ray. The present day name was granted to the suburb by its prominent and enthusiastic developer, Walter Burley Griffin. From the later half of the eighteenth century the vicinity was referred to as "Edinburgh Castle". Whether this was due to the existence of a rocky eminence visible from the harbour, or else accorded after the assassination attempt on the visiting Duke of Edinburgh in 1868, is not clear. Nonetheless the description of the rocky crag was contracted with the region's previous name to form "Castlecrag".

Despite its proximity to Sydney Cove, the coves of Middle Harbour remained unclaimed by Europeans until the mid nineteenth century. Mr J W Bligh received the first Castlecrag land grant in 1856-57. Albeit with the exception of a few scattered fisherman's huts, the region was left undeveloped for the next fifty years.

It was the vision of Chicago architect Walter Burley Griffin, which initiated the residential suburb of today. The eccentric yet likeable Griffin arrived in Australia in 1912 upon winning an international competition for the design of Australia's Capital Territory. Although Griffin's plan was adopted by the Government, conflicts arose in its execution, and Griffin left Canberra for private practice in Sydney and Melbourne. In 1920 he sought investors and formed the "Greater Sydney Development Association", for the purpose of creating "Castlecrag Estate". His love for the Australian bush urged him to move to Castlecrag shortly after the company's formation. The influence of his early practice partner Frank Lloyd Wright is recognisable in Griffin's unique modernist residential designs. He strove to incorporate and optimise the natural surrounds (rock, bush, light, and water) with the dwellings. Of his twenty residential designs, fifteen were built.

Griffin's wife Marion, a competent architect in her own right, shared Walter's enthusiasm for the community of Castlecrag. They initiated many social and cultural community projects, including the "New Haven Scenic Theatre". The Australian bush leant a truly unique setting for dramas and classics which attracted much interest from far afield. The open air classical amphitheatre remains today as a legacy of these histrionic occasions.

Economic and mainstream aesthetics ran contrary to Griffin's enthusiasm. Many considered his designs eye sores, and the Depression effectively halted all further development of his project. In 1936 Walter and Marion left their Castlecrag home for India, and a new architectural project.

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