Early Life
Cherry was born on 4 June 1895 at Drysdale, Victoria, to John Gawley Cherry and his wife Elizabeth, née Russel. When he was seven years old, the family moved to Tasmania and took up an apple orchard near Cradoc. Cherry attended the local state school until he was thirteen, after which he received private tuition. He worked with his father and became an expert apple packer; at fourteen he won a local case-making competition at the Launceston Fruit Show by packing thirty-five cases of apples in an hour. Joining the Australian Army Cadets in 1908, Cherry soon became a sergeant and later a second lieutenant, where he used to drill cadets in four different districts. At the age of sixteen, he won the President's Trophy and Gold Medal for being the best shot at the rifle range in Franklin. He also rowed with the Franklin rowing club, played the cornet in the Franklin brass band and sang in the Anglican church choir. In 1913, Cherry joined the Citizens Military Force and was commissioned into the 93rd Infantry Regiment as a second lieutenant.
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