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Ann, born in 1862, was the eldest child of John MacLeod and Ann MacAskill of 18 Ruisgarry (Brusda), then Quay. She became a domestic servant and married Donald Taylor MacAskill of Ferry in 1885. They did not have any children. Her husband passed away in 1909 and Ann continued to live at Port, working as a wool spinner.
Her young neighbour, Donald MacKillop recalled Ann in his book Coille an Fhàsaich:
There was one big strong widow in the Port, Anna Iain Mhòir, who used to fill the window of her bedroom with dry seaweed for the winter. This protected her window so well that she never even heard the winter storms. She was a funny old lady...
In an article he wrote for the Stornoway Gazette in 2002, he wrote:
The double house ... was occupied by two widows, Maggie née MacMillan, and Anna, née MacLeod. They both had hen houses and were always quarrelling about the hens. Anna was a big imposing lady, but very kind to the local children, who nicknamed her 'The Moderator of the Free Church of Scotland', of which she was an adherent. She had a strong, deep contralto voice, and the children used to listen to her at night, precenting the Gaelic psalms before she went to bed. When some person told her nickname (to annoy her) she was justly proud of it, saying that she could not have been baptised with a better name ...
In later years Anna moved to Grenitote, where she lived with her step-sister Ann.