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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).

File consists of Winsom's business cards, member cards, badges, and name cards for events and speaking engagements. Includes three business cards, a CARFAC member card and five name cards relating to events and talks, such as the Dagara Shamanic African Diaspora Training (2003-2004) and the Belize International Film Festival (2005).

File consists of photographs of a workshop led by 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 newspaper clippings and articles relating to the honorary doctorate Winsom received from OCADU in 2015.

File consists of two photographs and two printouts of images of Winsom's works, including textile and artworks.

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 contains personal records relating to Winsom's travels and activities. Includes a photocopy from a Belize travel guide, a flyer for Whisky Hill Craft Gallery, records relating to celebration of life services for Madgery and Leonard Gardner, and other event invitations and travel records. Also includes a series of loose pages of math notes that are unlabeled, but are possibly Winsom's schoolwork, or work that she graded as an instructor.

File consists of Winsom's photo albums. Includes an album of photographs from Winsom's youth, textile works designed by Winsom, and school workshops led by Winsom.

File consists of Winsom's photographs. Includes photos of Winsom's art and textile works, Winsom in her studio, family and friends, photographs from Winsom's speech at OCAD University when she was received an honorary doctorate degree in 2015, and other events and workshops.