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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 to solicit the letters, invitations to a party that was held at A Space Gallery to celebrate the occasion, and a number of pages where guests wrote notes to Winsom. One of Winsom's headshots is attached to the cover of the binder.

File consists of an event menu, invitations, newsletters, and other material featuring art and illustrations by Winsom. Includes the Kingston Jamaica YMCA Camp Councillor's Training Manual featuring Winsom's illustrations and the premier issue of the Jamaica Pat Boone Magazine, which includes a short story by Winsom on page 13, as well as a note across pages 14-15 reading "my page."

File consists of 16 pages of sketches and illustrations by Winsom, as well as one dyed textile work of Winsom's name glued to paper. Includes pattern designs, cards, motifs for fabric, and other sketches. Materials are predominantly undated.

File consists of newspaper clippings, articles, and related publicity material. Includes clippings regarding school workshops, arts education, and other events and projects that Winsom was involved in regarding art, activism and community organizing, among other topics. Includes records relating to Queens's University,

File consists of newspaper clippings and articles relating to the honorary doctorate Winsom received from OCADU in 2015.

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 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 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 posters, flyers, brochures, and other textual records relating to Winsom's exhibitions, workshops, and other early projects. Includes records relating to Black Wimmin: When and Where We Enter (1989), Afro-Jamaican Fabrics (1985), Into the Heart of Africa (1990), and Exhibition of Works by Jamaican Artists (1973), among others.

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.