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File consists of records relating to Winsom's work in schools and classrooms as a visiting artist, and associated grant applications and reports.

File consists of programs, conference booklets, and related printed material regarding conferences Winsom attended and contributed to. Includes records relating to Preserving our Heritage: Black Awareness Conference (1988), It's A Cultural Thing (1992), Vital Links: Enriching Communities Through Art & Art Through Communities (1997), Writing Thru Race Conference (1995), "Mothering in the African Diaspora: Literature, History, Society, Popular Culture and the Arts (2000), the 8th International Congress of Orisa Tradition and Culture (Havana, Cuba, 2003), and others.

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 Fresh Voices: A Collection of Poetry, Short Stories and Script by the Fresh Arts Creative Writing Program of 1993. Winsom was an instructor and founding member of the Fresh Arts collective, which was founded in 1992 with the goal to establish a Black artist-led youth mentorship program. The booklet is addressed to Winsom on the inside page and contains handwritten messages and signatures from the student participants.

File consists of records relating to Draw it Black and the Draw it Black Artist's Collective (DIBAC), a not-for-profit group dedicated to promoting the work of African Canadian artists. Includes a copy of the Draw it Black publication, promotional material for the launch of the publication, an issue of the journal Lola (Winter 2000-2001), which references Draw it Black on page 72, copies of a published interview with Winsom regarding the project, clippings from printed material, and other related documents. Also includes a portfolio folder with a sticker for the launch of Draw it Black on July 13, 2000, which contains a flyer for the River of Life exhibition, a summary of four of Winsom's exhibition projects in 2000 and a page of biographical information.

File consists of records relating to the Winsom Foundation, a Belize-based non-profit organization established by Winsom in 2007.includes printed material such as a brochure, flyers, and event posters, an Art Journal by the Art Students of Cristo Rey R.C. School (a project that was supported by the Winsom Foundation), as well as correspondence, a certificate, and a form relating to a tour of the National Institute of Culture and History (NICH). Also includes a copy of the publication This is How We Keep Breathing: Voices from Belize & Beyond..., which is an anthology of poetry and short stories resulting from a collaboration between OCAD U and the Winsom Foundation. Winsom also contributed writings and illustrations to the publication.

File consists of photocopies of pages from a guestbook with visitors' notes and signatures for the exhibition Weapons of Culture (1988), held at the A Space Gallery in Toronto.

File consists of a guestbook with visitors' names and comments from a variety of exhibitions and festivals that Winsom participated in. Includes comments from the Harrison Festival of the Arts, the Festival of Friends, the Festival of Nations, Roundup 1992, and other projects.

File consists of records relating to the Harrison Festival of the Arts in Harrison Hot Springs and Winsom's related exhibitions and projects. Includes six programs for various years (1988, 1989, 1992, 1993,1995, and 2001), visitor comments, a flyer, correspondence, and itinerary material. Also includes two copies of "Idi Na Otu," an Exhibition of African and Canadian Works that was shown in Vancouver and at the 1995 Harrison Festival of the Arts.

File consists of a story titled "The Mirror of Dearth," and an excerpt from "A story from Asante," telling the story of Ananse the Great Spider. This story relates to research for Winsom's textile artwork, "The Mirror of Dearth" (1995).