The series comprises subject files covering the Massey Foundation's most important projects, including Massey College, the Crafts Collection, Garnons Convalescent Home, Hart House, Massey Hall, Upper Canada College chapel, the National Gallery of Canada, the Stratford project (Avon theatre), the Massey Medal for Geography, and the Vincent Massey Awards for Excellence in the Urban Environment. In addition, there are files on other subjects or themes of interest to the Foundation's work.
The projects with the richest documentation are Garnons, Massey College, and the Crafts Collection. Documentation related to Garnons, the convalescent home in Hertfordshire for Canadian military officers during the Second World War, includes correspondence, financial records, inventories, and a wide variety of registers and log books. The records reveal the minutiae of running the Home and preserve the names and personal information relating to the officers, staff and visitors who were there during the war. The Massey College files document the origins of this ambitious project at the University of Toronto and its execution; they also bear witness to the ongoing, and sometimes difficult, relationship between the College and the Foundation. There is much interesting correspondence in the files between Masters of the College like Robertson Davies and Chairs of the Foundation such as Vincent Massey and Hart Massey.
Subject files also document Hart Massey's passion for Canadian crafts. He devoted tremendous time and energy to building up the Massey Foundation Crafts Collection, which he ultimately donated to the Museum of Man (later the Canadian Museum of Civilization). The files contain valuable information about the craftsmen and craftswomen and their works, and the process by which the Crafts Collection acquired these works. The series also holds textual records and sound recordings relating to John Flanders' book "The Craftsman's Way: Canadian Expressions" (Toronto: University of Toronto Press, 1981) which had an introduction written by Hart Massey. There are twenty-two audio cassettes of interviews conducted by John Flanders with men and women featured in the book.
In addition, this series contains a drawing by Alan Beddoe of the Coat of Arms for Massey College and an over-size certificate presented to H. A. Massey by his employees on the 40th anniversary of the Massey Manufacturing Company (vol. 27) in 1887.