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File consists of flyers and other promotional material, an exhibition catalogue, and a comb-bound booklet of photocopies of reaction cards relating to Entering the Millennium: A Spiritual Dialogue (1997), an exhibition at the Art Gallery of Ontario.

File consists of print material relating to three artistic projects, This is Not a Poem: This is A Summer Quilt (1994), Head Above the Water (various), and Painting up a Storm (1998). Includes promotional material such as flyers, programs and invitations as well as a page of correspondence relating to Head Above Waters - Four Aspects, and an issue of Ontario Craft magazine (May/June 1996) featuring an article on page 20 regarding "This is not a Poem, This is a summer quilt."

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 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 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 posters and other promotional material relating to Winsom's exhibitions and other projects featuring Winsom's work, including "uhuru sasa/ freedom now" (1991) and Black Wimmin, When and Where We Enter (1989). Also includes a brochure for "Toronto Tributes + Tributaries 1971-1989" (2016).

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 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 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.

File consists of records relating to Winsom's solo exhibition, I Rise (2019), held at the Art Gallery of Ontario. Includes installation documents, crate lists, budget documents, and related exhibition documents.