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File consists of a handwritten letter from a teacher and photographs from a workshop Winsom led at a school.

File consists of colour photographs signed by Winsom.

File consists of photocopies of reflections written by students in response to a presentation given by Winsom for a group of students in New Jersey.

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

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 contains a binder that was made for Winsom's 50th Birthday, containing notes and letters from friends and family. Includes the letter that was send out to solicit the letters, invitations to a party that was held at A Space Gallery to celebrate the occasion, and a number of pages where guests wrote notes to Winsom. One of Winsom's headshots is attached to the cover of the binder.

File consists of an event menu, invitations, newsletters, and other material featuring art and illustrations by Winsom. Includes the Kingston Jamaica YMCA Camp Councillor's Training Manual featuring Winsom's illustrations and the premier issue of the Jamaica Pat Boone Magazine, which includes a short story by Winsom on page 13, as well as a note across pages 14-15 reading "my page."

File consists of 16 pages of sketches and illustrations by Winsom, as well as one dyed textile work of Winsom's name glued to paper. Includes pattern designs, cards, motifs for fabric, and other sketches. Materials are predominantly undated.

File consists of newspaper clippings, articles, and related publicity material. Includes clippings regarding school workshops, arts education, and other events and projects that Winsom was involved in regarding art, activism and community organizing, among other topics. Includes records relating to Queens's University,