Allan "Dempsey" Henwood was born at Whitemark on 9 October 1920 and was raised on Flinders Island, where his family was well known through farming and business. His brother, Eric Henwood, also became a soldier settler on the Furneaux Estate. Dempsey enlisted in the Royal Australian Air Force in July 1941 as an Aircraftman First Class (AC1), serving for four and a half years, including postings in Darwin and the Northern Territory. He was discharged as a Corporal on 23 January 1946.

After returning to Flinders Island, Dempsey took up Lot 3 at Kentdale and married Betty soon afterwards. Although the farm struggled in its early years and required boundary adjustments before it became viable, he worked hard alongside neighbouring settler Percy Anderson. Away from farming, he enjoyed "birding" trips to the offshore islands to catch mutton birds. Despite their efforts, the property never developed into a financially viable farm, and the family left Kentdale within a decade.