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Kenneth MacAskill was born in 1870, the eldest son of Peter MacAskill and his wife Lexy Ferguson of 4b Ruisgarry (Tarraloch), which passed to him on his father's death in 1917. His cousin Murdo MacAskill later passed Kenneth 4a Ruisgarry (Tarraloch), so the two parts of the original croft were recombined.
Kenneth became a fisherman, then a yachtsman, as did many of the Berneray men in the early years of the 20th century. He was also a crofter. Kenneth married his wife Lexy MacKillop in Glasgow in 1898, and they had eight children together. Three of their children emigrated to Vancouver, and their youngest son, Kenneth John, was killed during the Second World War.
On Kenneth's death in 1945, 4 Ruisgarry (Tarraloch) was passed to eldest son Peter.