Whitehead was head 1937-9 of the vocal department at the Bornoff School of Music. She moved to Kenora, Ont, in 1949, but commuted to Winnipeg to continue teaching privately and at the Mennonite Brethren Bible College 1952-7. She conducted three choirs in Kenora: the G Clef Ladies Choir, which achieved prominence throughout western Canada in concert and festival appearances; the Community Choir of Kenora, a mixed choir of 65 voices that presented major choral works; and the St Alban's Anglican Cathedral choir. She was an itinerant lecturer 1957-61 for the Ontario Department of Education, travelling to various communities from Thunder Bay to the Manitoba border, and she commuted 1962-7 between Winnipeg, Thunder Bay, and Kenora every week to teach privately. In 1968, moving to Hamilton, she was appointed principal of the Royal Hamilton College of Music, remaining in that position until 1975. She was a teacher of vocal and choral techniques 1967-74 and a voice instructor 1971-8 at McMaster University.
She examined for the RCMT, the WBM, and the University of Western Ontario and from 1954 to 1989 adjudicated competition festivals across Canada. For four years she adjudicated at the Bahamas and Out Islands Music Festivals. She was president of the RMT of Winnipeg 1940-4 and the ORMTA in Kenora 1958-65. She was a member of the Canadian Music Festival Adjudicators' Association 1976-9, the Federation of Canadian Music Adjudicators Association 1954-89, and the ORMTA Council for Hamilton and area 1978-82. She was a contributor to EMC.
Her pupils included Evelyne Anderson, Devina Bailey, James Bechtel, Paul Coates, Orville Derraugh, Marilyn Duffus, David Falk, Victor Godfrey, Catherine Henry, Peter Koslowsky, Helen Litz ( Mennonite Children's Choir), Nona Mari, John Martens, Victor Martens, Melanie Mathews, Marjorie Patterson, Maxine Miller Pinker, William Reimer, Wilmer Neufeld, Phyllis Cooke Thomson, and George Wiebe. The Gladys Whitehead Scholarship was established by the John Laing Singers and Wilfrid Laurier University in 1986.
Whitehead was married to Bill Whitehead, a farmer. Their daughter Sheilagh married Richard Cohen, a french hornist with the TSO.
Author Frederick A. Hall, Barbara Norman, Betty Nygaard King
'Gladys Whitehead,' Sharps & Flats, vol 6, Nov 1965
Fraser, Hugh. "Gladys Whitehead was musical pioneer," Hamilton Spectator, 18 Oct 1995

The Toronto Maple Leafs’ victory in the 1967 Stanley Cup was a singular event. Who would have predicted that it would not happen again?
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