As a friend of Phyllis Porteous and her family of ten brothers and sisters, Gwendolen Marjorie Howard also befriended their relatives, the Drury family from Kingston, Ontario. Mrs Porteous was born Frances Eliza Drury in Kingston in 1857. Her older brother was Major-General Charles W. Drury (1856-1913). Prior to the South African War, the then Lieutenant-Colonel Drury commanded the Permanent Force artillery at Kingston. Following the war he was appointed military commander of the Maritime Provinces region and was based in Halifax. In 1905-06, his command took over the large fortress at Halifax from the departing British garrison. This placed him in charge of the largest military establishment in Canada.

Identified in several of the collection's photographs as "Toddles," Major-General Drury had six children: Edith (b. 1881); Victor (b. 1884); Gladys, (1885-1927) (future wife of Lord Beaverbrook); Louise Emily Arabella (b.1886); George Chipman (b. 1888); and Helen (b. 1896). As is evidenced by the photographs in the collection, Miss Howard spent several vacations with members of both the Porteous and Drury families at the Porteous family home on Île d'Orléans, at Métis-sur-Mer, and at the Drury family home at 107 King Street in Kingston. In addition, according to documentation found in the archives of McGill's Osler Library, Miss Howard's relationship to the Drury family could well have become much closer since she was at one point engaged to Victor Drury.

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