Winnie was born in Rosenfeld, Manitoba in 1911, as Winnifred Kathleen Weber. Her father came from Alsace, France and her mother from Clinton, Ontario. The family moved from Rosenfeld to Winnipeg in 1918, changing their surname to "Webber" to ensure dad could get work during the Great War, then moved to Calgary in 1923. Winnie got her business college certificate five years later, then married Albert Benedict in 1930. They raised three children; two boys and one girl.
Winnie and Albert were very sociable, starting the Orion Club in the 1930's for young adults and keep the friendships through bridge nights and parties. The family grew up in the Thorncliffe district and were very involved in community events, especially the senior's group. Winnie worked until 82 and passed away at age 91.