Isabella was the daughter of John Macaskill and Isabella Macleod of 46 Upper Carloway. She married Donald Montgomery, 7 Arivruach and they left the island for Windsor, Ontario. They returned to Scotland and lived in Glasgow for a period before moving to Arivruach where they opened and ran the first Post Office from 1950 to 1952. They then spent some time in Australia before returning to Scotland and living in Alexandria. They had four children.