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File consists of photocopies of visitor comments relating to an unspecified exhibition of Winsom's work at the A Space Gallery in 1998.

File consists of records relating to Winsom's solo exhibition, The Masks We Wear (2022), held at the Agnes Etherington Art Center. Includes promotional material and other documents regarding the exhibition, including an itinerary and other travel documents.

Series consists of records relating to Winsom’s art and illustrations, such as original sketches, drafts, samples of printed material, and related documents. Includes programmes and postcards featuring Winsom's work, as well as published works including Granny and Me, a children’s book written by Gale Henry, illustrated by Winsom, and numerous editions of Everywoman’s Almanac, published by Women’s Press and featuring illustrations and text by Winsom.

Find consists of a binder of slides, predominantly photographs of Winsom's artworks and exhibitions, as well as Winsom's work at schools and the works of a number of other artists. Includes photos of River of Life, OYA and Total Universe, as well as the Lawrence Height Middle School and Queen Victoria (school), among others.

Series consists of records documenting Winsom’s work as an arts educator and mentor to young people, as well as her involvement with a variety of community organizations as a founder, member, or contributor. Includes newsletters and other printed material, grant applications and reports relating to Winsom’s work in arts education, promotional material for talks and workshops led by Winsom, and related textual documents. Contains records relating to Winsom’s work with the Kingston Black Women’s Collective, the West Indian Canadian Association, Draw it Black, Fresh Arts, and the Winsom Foundation.

File consists of records relating to Winsom's work as an arts educator, especially relating to talks, workshops, and discussions. Includes promotional material such as programmes, flyers and posters and related documents such as schedules.

File consists of audio-visual material relating to Winsom's exhibitions and projects. Optical disks contain a digital catalogue for Rousings (2004) featuring Winsom's artist statement, video footage from the opening of Iconography of Divination (2003) at the A Space Gallery, and "OYA + Yemaya," a movie by Winsom. Also includes the movie All Eyes on Africa (1993) by Clem Marchall on VHS and a VHS tape titled "Interview Grand Cayman - Looking for perfect teachers 2004."

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 records relating to Winsom's exhibitions and other projects in Belize. Predominantly includes promotional material and related documents for exhibitions in Belize, including Women in Art (2011, 2015, 2016) and 29: Artists, Works, Years. Also includes records relating to the Belizean Women's Art Collective, who were mentored and inspired by Winsom.

File consists of clippings and printouts from publications relating to Winsom's exhibitions, activities, and community work in Belize. Includes material relating to I Am The Alchemist (2007), Winsom's work with the Cristo Rey Primary School, the Women in Art exhibition(s) organized by the National Institute of Culture and History (NICH), and other projects. Also includes an issue of the magazine BAFFUprinted, 2016, which features an article about an organization Winson was involved with in Belize.