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File consists of undated portraits and headshots of Winsom, as well as related contact sheets and film negatives.

File consists of photographs of a workshop led by Winsom at a school.

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 records relating to Winsom's work in education and with community organizations. Includes records relating to her work with the YMCA, the Jamaica National Commission for UNESCO, the West Indian Canadian Association, her campaign for School Board Trustee for the St. Lawrence Ward, the May Pen Day Care Centre, and the Kingston Black Women's Collective. Also includes a signed poster of author and activist Angela Davis, addressed to Winsom.

File consists of newsletters, articles and other print material regarding organizations and other community efforts that Winsom was involved with. Includes newsletters and other printed material from CARFAC, Canadian Woman Studies (York University), and the Women's Resource Centre (Grand Cayman). Also includes an undated work of writing titled "Systemic Barriers Faced by Black Artists," (1999?), possibly relating to a discussion of the same name in which Winsom was a key speaker, "Coming in from the outside: Winsom's technology of Voudun" by Nalo Hopkinson, and the premiere issue of Possibilitiis [sic], a literary arts magazine, which includes Winsom in the "Editor's thanks" list on page 4.

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.