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This sous-fonds is comprised of correspondence and legal documents pertaining to insurance, loans, mining leases, promisory notes, the Cataraqui Bridge Company and the Kingston Hoisery Company. There are also a large number of documents reflecting the many land transactions in which Simpson was involved. Of particular interest are the records pertaining to Farm Lot 24, Lot 23 and Lot 16 (Military Reserve) in the City of Kingston.

The sous-fonds mainly consists of records regarding land lots, sales and transfers in the Provinces of Ontario and Manitoba. It includes bonds, deeds and indentures, accounts connected with the estate, and powers of attorney. Also included are some documents reflecting Machar's involvement with the Canadian Mica Company, the Midland District Schoolboard and the Rideau Canal.

The sous-fonds consists of personal papers, correspondence, business papers, legal documents and documents relating to the settlement of the estate, and land records relating to land lots owned by Maitland. Of particular note are the personal papers which contain military commissions for Maitland.The material has been arranged chronologically within the series and the correspondence has been indexed according to date and author/recipient.

Sous-fonds consists of a typescript for "The poetry of E.J. Pratt: A new interpretation."

Sous-fonds consists of a holograph poem, titled "Requiem."

Sous-fonds consists of a holograph poem, titled "The Last Invocation."

Sous-fonds consists of drawings and a test print of the front cover for Charles G.D. Roberts "The Iceberg and Other Poems."

Sous-fonds consists of manuscripts and page proofs for "Book of the Seasons," "Song of the Prairie Land," "The Castle of Graymoor," and "Old Loves Are Best."

The sous-fonds consists of a typescript for "Dog Monday's Vigil" with holograph notes, adapted from Rilla of Ingleside.