Like his brother Willoughby Baynes Huddleston, at the age of 7 he was sent to Bedford Modern School which he attended between 1881 and 1888, leaving the school at fourteen to join the Merchant Navy.
He was later Shipping Surveyor and Adviser to the High Commissioner for India and Aide-de-Camp to the Viceroy. Having joined the Merchant Navy in 1888, Huddleston received his certificate as Second Mate of a Foreign Going Ship on 30 May 1895. He then joined the Royal Indian Marine initially serving in the Egyptian Campaign.
He took the Officer’s course at the Royal Naval College, Greenwich and in 1897 was in the troopship, Warren Hastings, when she was wrecked at sea off the coast of Mauritius.
Huddleston served in the China Expedition against the Boxer Rising (1901-1902). During World War I he served as senior marine transport officer of Bombay.
He was promoted to Captain in 1918 and was Presidency Portuguese Officer of Madras before being appointed Deputy Director of the Royal Indian Marine in 1924 and officiating Director for some months in 1925. Huddleston then served in the Indian Civil Service as shipping surveyor and adviser to the High Commissioner for India in London.
He was at one point aide-de-camp to the Viceroy, Lord Reading.
Huddleston was placed on the retired list of the Royal Navy in 1934 and was knighted in 1939. On 4 August 1904, Huddleston married Elsie Barlow-Smith. They’d met in Bedford as school children.