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• Consists of five volumes of diaries written by Orr in Montreal, Hamilton and other centres in Eastern Canada; and four volumes written in Calgary.
• 1893-1894 diary. The entries discuss the weather, his social activities (the Opera House, concerts, plays, circus, etc.), the activities of his son Lorne, the incorporation of Calgary as a city, his campaign and election as Mayor, City Council duties, and his activities in overseeing public works such as the development of the city’s electrical system.
• 1895-1896 diary. The entries discuss the weather, social activities, a trip to Eastern Canada, activities of his son Lorne, duties on Calgary City Council, and his defeat by two votes for another term as Mayor.
• 1896 diary. The entries discuss the weather, his social activities, the activities of his son Lorne, and his City Council duties.
• 1897 diary. The entries discuss the weather, his social activities, the activities of his son Lorne, his duties as Mayor (he was elected by acclamation in 1897), and the development of the City of Calgary.

Consists of logs of journeys, probably belonging to his father Franklin Haultain; notes about the 1877 Blackfoot Treaty (Treaty 7); articles about Haultain’s hat; an articles on the Knight Bachelor Order; and various notes and envelopes.

Consists of silhouette at age four (1849), letter to his father as child (ca. 1851-1955), and letter to his mother as a child (1856).