Fitzgerald was born on February 16, 1914, at White Point, Victoria County, Nova Scotia, a remote fishing village on the northeastern tip of Cape Breton Island.
During this time, Fitzgerald played radio shows and tours with Hank Snow for about two and a half years.
In 1947, he formed a group called the "Radio Entertainers" with Beattie Wallace (piano) and Estwood Davidson (guitar).
Many of Fitzgerald's recordings are now out of print, but a selection culled from his albums has been reissued as Classic Cuts by Breton Books & Music.
A significant portion of his repertoire has been preserved in a book called Winston Fitzgerald: A Collection of Fiddle Tunes, issued by Cranford Publications.