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Kenneth was born in 1876, the eldest child of Angus MacAskill and Marion Munro, cottars on 11/12 Ruisgarry (Quay). In 1891 Kenneth was registered with his uncle Donald’s household in Quay. Kenneth and his parents moved to newly allotted 6 Borve in 1900.
In 1901 Kenneth was working as a farm grieve, before becoming a yachtsman by the time of his marriage to Christina MacLeod in 1909. Later he worked as a fisherman. The couple lived at 6 Borve for two years, before moving to their new home at Rhuvanish. They had five children together.