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File consists of Winsom's personal and professional correspondence, predominantly cards and postcards received from friends and family. Includes Birthday, holiday cards, thank you cards, travel postcards, and other correspondence.

File consists of Winsom's personal and professional correspondence from approximately the mid- to late-1990s. Includes correspondence relating to Winsom's exhibitions, speaking and writing projects, grant applications, art education, and other topics. Also includes three photographs that were interfiled in Winsom's correspondence.

File consists of Winsom's personal and professional correspondence. Includes correspondence relating to exhibitions and other projects, grant applications, art education, and other personal topics and professional projects.

File consists of Winsom's personal and professional correspondence, predominantly relating to her time living in Belize. Includes correspondence relating to the Winsom Foundation, exhibitions such as Jumping the Big Boa (2012), and more.

File consists of a copy of Panic Poems by Katie Usher. On the front page is a hand-written note to Winsom reading "To: Dr. Winsom Winsom - my art mother, my mentor, my light [...]."

File consists of personal and professional correspondence relating to Winsom's life and work. Includes material regarding her work in education, including her work with the Jamaica National Commission for UNESCO, thank you letters from students, as well as personal and birthday letters. Also includes correspondence relating to her research in Ghana under the Canadian Arts Council Aid, and other projects.

File consists of correspondence, predominantly thank you notes and letters regarding Winsom's work. Also includes some correspondence relating to grants and funding for Winsom's projects, art donations, and related correspondence.

File consists of Winsom's personal and professional correspondence. Includes correspondence relating to exhibitions and other artistic projects, grant applications, art education, and other topics.

File consists of an autograph notebook containing notes and letters written to Winsom throughout the 1960s.

File contains professional documents relating to Winsom's work. Includes professional correspondence, a CV, loan agreements for exhibitions, meeting notes, release forms relating to two editions of the publication Canadian Who's Who, budget documents, and other related documents.