Before coming to Victoria, Caroline spent time living in India with her sister, to look for a British Officer to marry. She never found one there.
In 1863 Caroline Trutch married Peter O'Reilly. For the first few years of their marriage Caroline and Peter moved back and forth between Victoria, Yale, and New Westminster.
When Caroline was expecting her second child she wished to establish a permanent residence in Victoria in order to be close to her family. It was Carolines responsibility for the day to day running of Point Ellice House. From the hiring of the servants, to maintianing the kitchen and planning of dinner parties and social events held there.
Caroline was said to be a well educated woman, and have an astounding singing voice. Many evenings she and Kathleen would sit in the parlour and play Duets together, Carolyn on the piano and Kathleen on the harp.
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