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The fonds consist of photographs depicting life in Chesterfield's postings within the Hudson Bay district, such as Moose Factory, Fort George, Great Whale River, and Rigolet on the Labrador coast. Included also are images depicting Montreal buildings, agricultural scenes from the area, various public events which took place, such as government announcements. There are photographs of the Ile d'Orléans, where Chesterfield felt there had been a return to "simpler" times. Also he took various photographs of tourist attractions around Canada, such as Hamilton Falls, Ontario and Montreal winter scenes, and images of maple syrup being made. There are also some selected images he took while he worked as a general press photographer of important events, such as the visit of the Prince of Wales to Canada in 1923. Included in the collection are [portrait] photographs of Inuit and Cree, he took these as both an observer of tradition and as fur trapper. In one of his albums there are images of Canadians preparing for WWI featuring various government officials, and many different battalions from Ontario and Montreal. There are also photographs of Mr. Chesterfield himself. The fonds also contain manuscripts written himself describing life as a fur trader, the various cultures he encountered and his interactions with different peoples as well as his opinions of them, and personal comments and descriptions of some of his photographs.

The records start with the proceedings of the first town council in 1838 and are continually being acquired. Many of the early minute books are indexed. In addition there are separate volumes for committee reports between 1842 and 1898, and for bylaws between 1838 and 1907. The minute books and correspondence of the Finance and Accounts Committee are of interest. The story of the Fire Department between 1888 and 1936 is to be found in the records of the Committee on Fire and Light. There are scattered records for the Parks and Property Committees, fairly detailed records for the Board of Works between 1891 and 1936 and for the Board of Health around the same time. The correspondence of the City Clerk is complete from 1898 to 1938 and there are letter books from 1952 on as well as scattered letter books from 1852 to 1896. The records of the City Treasurer comprise an extensive collection of account books as do the records of the City Engineer.

The fonds consists of correspondence, scrapbooks, news clippings, transcripts of local diaries, and alphabetical family and genealogical files. These genealogical files, which relate mainly to Bay of Quinte and Loyalist families, contain correspondence, research from printed sources, newspaper clippings and some photographs. Also included is a set of ordnance survey maps of Kingston and area dated 1869.

The fonds consists of architectural drawings and accompanying project files reflecting the solo career of Lily Inglis including projects she undertook in England, Italy, Philadelphia and Kingston. The drawings consist of tracing paper originals, pencil sketches, diazotypes, acetates, sepia diazoa and black line prints of a variety of different sizes.