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File consists of Winsom's personal and professional correspondence, predominantly relating to her time living in Belize. Includes correspondence relating to the Winsom Foundation, exhibitions such as Jumping the Big Boa (2012), and more.

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 contains a 1990 issue of CRAFTS Plus, which features an article on textile dying on page 32 that Winsom contributed to, a 1998 issue of WORD magazine featuring quotes from Winsom in an article on page 20 and a reference to Winsom's exhibition "Painting up A Storm" on page 36, and the premier issue of Dream World magazine (2011?), featuring Winsom on page 7 in a section titled "Canada's Most Prominent Black Women." Also includes a page of correspondence to Winsom from the Assistant Editor at CRAFTS Plus Magazine regarding her contribution, a photocopy from WORD, and a clipping from a separate issue of WORD magazine featuring event information about Winsom's exhibitions.

File consists of clippings and printouts from publications relating to Winsom's exhibitions, activities, and community work in Belize. Includes material relating to I Am The Alchemist (2007), Winsom's work with the Cristo Rey Primary School, the Women in Art exhibition(s) organized by the National Institute of Culture and History (NICH), and other projects. Also includes an issue of the magazine BAFFUprinted, 2016, which features an article about an organization Winson was involved with in Belize.

File consists of newspaper clippings, articles, and related publicity material published in approximately the 2000s, relating to Winsom's professional work and activities. Includes press material relating to the Marilyn Lastman award for excellence in art awarded to Winsom in 2002, the exhibitions A Sign of the Spirit, Iconography of Divination and For My Mother: A Visual Prayer/feast, an artist profile on Winsom, and other projects and activities.

File consists of a red-colour scrapbook made by Winsom containing press clippings, as well as some correspondence and other textual records. The press material in the scrapbook covers a variety of topics and events, which predominantly document racism and instances of discrimination in Canada and especially in the Kingston, Ontario region.

File consists of newspaper clippings, articles, and other publicity material relating to Winsom's work and activities, published in the year 2000. Includes publicity material relating to the River of Life (2000) exhibition, Draw it Black, an interview with Winsom in the Toronto Star, and other projects.

File consists of clippings and photocopies of a 1988 Toronto Star article written by Christopher Hume titled "Black artists enter the Toronto mainstream," which includes references to Winsom's involvement in the Weapons of Culture exhibition at A Space Gallery.

File consists of newspaper clippings, articles, and other publicity material relating to Winsom's work and activities in the 1990s.

File consists of newspaper clippings and articles from publications based in the Cayman Islands. Includes press relating to the exhibition, Rousings (2004) and Winsom's workshops at the Cayman Island's National Gallery.