This diary was started by Canby A. Alexander in January 1883, when he was 10 years old. At 10, Alexander was no longer enrolled in school but instead was occupied with the family farm and the comings and goings of his extended family, neighbors and friends. Alexander lived with his sister Sallie and widowed father, who earned additional income butchering cows and hogs near Brick Meeting House, Maryland, the town of Rising Sun nearby. The diary's owner noted his father's activities including his regular trips in and out of town to Oxford, and Nottingham in Pennsylvania; Wilmington and Bayview in Delaware; and Lombardville and Mount Olivet in Maryland.

By the age of ten, Alexander had assimilated the county's social hierarchies and relative status of the folks with whom he came in contact. His understanding of Cecil County's pecking order was encapsulated in the phrases he penned: "Mr. and Mrs. [John] Algard was here today"; "Cousin Dave was here this evening"; and "the Darkeys finished whitewashing." The three-day per page diary helped the young boy reduce the world around him to succint entries.

The contrast between the daily round of farm chores and the bustle of commercial activity away from the family farm must have stirred young Alexander's interest in being his own boss. By 1895, he was totalling up profits from rents from his properties. As of July of that year, he had not yet reached majority. The Alexanders may have been descendants of Robert Alexander, once a delegate to the Continental Congress, who later defected to the Royal Navy. His estate became the town of Elkton, Maryland.