Early Life
Middleton was born in Waverley, Sydney on 22 July 1916, and spent his early years in the Central Western district of New South Wales. He was a great-nephew of the colonial explorer, Hamilton Hume. He was an athletic young man, and excelled in cricket and Rugby football at school. After leaving school, he worked for a time as a jackaroo at Leewang station, the large grazing property his father managed.
He enlisted in the Royal Australian Air Force on 14 October 1940, and trained as a pilot in the Empire Air Training Scheme. He undertook initial flying training at No. 5 Elementary Flying Training School (5 EFTS) Narromine NSW, and advanced training in Canada. In February 1942 he joined No. 149 Squadron of the Royal Air Force, flying as second pilot on Short Stirling bombers. By July of that year he was appointed as an aircraft captain, and flew his first raid as a pilot-in-command against Düsseldorf.
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