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.