Richard "Dick" Bayles was born in Hobart and had strong family connections with Tasmania, although he was living in Balgowlah, New South Wales, when he enlisted in the Royal Australian Navy on 6 September 1937 at the age of 18. Trained as a mechanical fitter, he served for twelve years in the Navy, including wartime service aboard several ships, and was discharged in 1948 with the rank of Chief Petty Officer. His final posting was to HMAS Bataan.

Following his naval service, Dick and his wife Peggy settled on Lot 2, where they farmed with their son, Leonard, until the mid-1960s. In the early years of the settlement, Dick supplemented the family's income by working for the War Service Land Settlement scheme as a fitter and welder, while Peggy drove the school bus that transported children from the settlement camps. After selling the farm, the family moved to Deloraine, bringing to a close their years as soldier settlers on Flinders Island.