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File consists of Winsom's personal and professional correspondence. Includes correspondence relating to exhibitions and other artistic projects, grant applications, art education, and other topics.

File consists of photocopies of reflections written by students in response to a presentation given by Winsom for a group of students in New Jersey.

File consists of an autograph notebook containing notes and letters written to Winsom throughout the 1960s.

File consists of Winsom's personal and professional correspondence, predominantly cards and postcards received from friends and family. Includes Birthday, holiday cards, thank you cards, travel postcards, and other correspondence.

File consists of Winsom's personal and professional correspondence from approximately the mid- to late-1990s. Includes correspondence relating to Winsom's exhibitions, speaking and writing projects, grant applications, art education, and other topics. Also includes three photographs that were interfiled in Winsom's correspondence.

File consists of Winsom's personal and professional correspondence. Includes correspondence relating to exhibitions and other projects, grant applications, art education, and other personal topics and professional projects.

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.