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Photograph is of five men saluting a ship. Four of the men are standing, and one is crouching, all are dressed in western style work clothing, and are standing on the edge of a cliff on the left said of the image. The Standing four are waving shotguns in the air. They are looking out to sea where there a large schooner is anchored.

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 album contains images taken in Chesterfield’s press photography days. Includes photos such as the collapsing of the Quebec bridge, and scenes of ‘typical’ Canadian life.

The series consists of albums of Chesterfield's travels in Northern Ontario, training exercises in the First World War, and photographs taken by Chesterfield during his time as a press photographer.

The album contains images depicting various military units in training, on the move, and getting ready to depart for the war at Valcartier. It also shows various government officials giving speeches and making announcements. Photographs are accompanied by newspaper clippings.

Photograph shows a landscape with a canoe with sails on water, there is one lone man sailing the canoe. Desolate landscape, only short vegetation, a slight hill in the background, and once again a plain white sky. The man has his back to the viewer, and he wears a hat pulled down over his jacket.

Photograph depicts Chesterfield kneeling in the snow under a fir tree. He is checking an animal trap, intended for small animals. There is an axe laying in front of him. The figures are spatially arranged in a diagonal line reaching from the bottom left hand corner to the upper right. This image is available in its original form or its flipped one.

Photograph is of a church seen behind a fence, in the middle of farm land at Moose Factory. The church is on the left of the image, while there are various fields with cows, and other buildings scattered throughout this image.