Winnie began her life in Cambridge, MA as the daughter of James and Winifred Boland. She spent the first 27 years of her life there and then married Thomas O'Callaghan on November 11, 1950 in St. John's Church. They later moved to Reading, MA and were there until 1972, when they moved to the Portland area. While the role of homemaker and mother took up most of her time, she also worked as a receptionist and swimming teacher. A Memorial Mass will be held at St. Francis Catholic Church, 1131 SE Oak St. Portland, OR. She is survived by her husband, Tom; her son, Sean; her daughters, Jeanne O’Callaghan, Michaela Bone, Ellen King and Colleen Elmquist. Winnie will also be missed by 11 grandchildren and 7 great-grandchildren. In lieu of flowers contributions may be made in her name to St. Francis Dining Hall.