Winnifred "Winnie" Olsen (nee Castle) was born on July 26, 1916 in Olympia, Washington. She attended and graduated from Washington State College (Washington State University) with a degree in sociology and journalism. She was involved in a number of organizations and causes including Red Cross, Girl Scouts, March of Dimes, United Good Neighbors, and many more. Winnie was also a writer and producer for a local Olympia Saturday morning radio show, “Mother Goose Radio Party”, from 1948 to 1957. Afterwards, she joined the Olympia High School PTA, City Council PTA, and the Citizens Advisory Council on Education.

She was also a member of the Olympia branch of the American Association of University Women (AAUW) for 60 years and was its president for two years. Along with this involvement, Winnie also helped to organize the Thurston County Juvenile Protection Committee and the Olympia Panhellenic Association. She wrote for the Olympia chapters of the YWCA, League of Women Voters, and Junior Programs.

Her career with Tacoma Public Schools began in 1967 and ended with her retirement in 1984. During this time, she focused on creating material that highlighted marginalized groups in the Pacific Northwest. She compiled over 100 years of information about the history of the Tacoma Public Schools for research for her book, For the Record: A History of the Tacoma Public Schools, 1869-1984.

After her retirement in 1984, Winnifred went on to volunteer around Olympia, serving at the Timberland Library, Friends of the Library, Thurston County Historic Commission, Washington State School Retirees Association, and others. In 1997, the Bush Family Interpretive Park was dedicated partially due to her extensive research on the history pioneer George Bush.

Winnifred died at the age of 94 in Lacey, Washington. She was awarded the YWCA Lifetime Achievement, WSU Alumni of the Year, Olympia High School Alumni Hall of Fame, Alpha Gamma Delta Distinguished Citizen, Olympia City Council Historic Preservation Award.