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File consists of records relating to Kindred Spirits: Winsom & Kofi Kayiga (2000), an exhibition at the National Centre of Afro-American Artists in Boston. Includes promotional material, a press release, and a document regarding three of Winsom's exhibitions in the summer of 2000, including Kindred Spirits.

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 records relating to I am the Alchemist (2007), Winsom's first major solo exhibition in Belize, held at the Image Factory art foundation. Includes promotional material and a Gallery Guide noting the locations for each installation in the exhibition.

File consists of promotional material relating to the exhibition Jumping the Big Boa (2012), held at the Image Factory art foundation in Belize.

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.

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 posters and other promotional material relating to Winsom's exhibitions and other projects, 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 contains a binder that was made for Winsom's 50th Birthday, containing notes and letters from friends and family. Includes the letter that was send out inviting people to participate, invitations to a party that was held at A Space Gallery to celebrate Winsom's Birthday, and party guests' notes to Winsom. Winsom's headshot is attached to the cover of the binder.

File consists of textual records relating to Winsom's grant applications and awards, as well as grant and award programs that Winsom sat on the jury for or participated in. Includes records relating to the Toronto Arts Council Foundation 2002 Awards, an invitation to a Gala Dinner for the Minister's Forum on Diversity and Culture (2003), a schedule for the ceremony relating to Winsom's Honorary Doctorate from OCAD University (2015), and related documents. Also includes records relating to Winsom's participation in the jury for the First Visual Arts Students Awards for the North York Board of Education in 1995, the Mid-Career Artist's Grant from the Ontario Arts Council in 1999, and a program for the 17th Annual Harry Jerome Awards in 1999. Winsom was commissioned by The Black Business & Professional Association to create a work for the Harry Jerome Awards, which is discussed on page 3 of the program under the title "The Fabric of Life."