David F. Cushing was born in Newfane, Vermont in 1814. At the age of 16, he journeyed to West Medway, Massachusetts where he learned the tailor's trade. There, he met and married Polly Adams (b. 1821), who gave birth to their first son Winfield in 1843. Shortly after his son's birth, Cushing returned to Vermont, establishing a general store in the village of Cambridgeport on the border of Grafton and Rockingham. He remained in business there for the next 56 years until his death in 1899.

In 1860, at the time of the daybook, Cushing had a household of eleven. It included his wife Polly; daughter Mary (age 12); sons Alverton (14), David Jr. (6), James (4), and Solon (3 months); a clerk, Frederick Barker (16); a domestic, Julia McQuade (16); Sally Brigham (66); and a schoolteacher/boarder, Lucy Eaton (20). Of his total of nine children, Cushing outlived five; he also outlived his wife by two years. In 1860, Cushing owned real estate valued at $4,000 and personal property worth $7,000. In addition to his general store, Cushing served as the postmaster of Cambridgeport and was deacon of the Congregational church.

Cushing's daybook reflects a fairly standard business in a small, rural community, relying on exchange as much as on cash. His stock, according to his own reminiscences noted in Lyman Hayes's History of the Town of Rockingham (1907), "comprised almost everything from a barrel of flour to a needle". To acquire his goods, he regularly traveled to Boston in an old-fashioned stagecoach, and he paid high rates for the transportation of his goods. Cushing also believed in taking care of his own business, having been "behind the counter nearly every day" since he started the store. The store, which eventually became one of the landmarks of Windham County, was a white building with green piazza posts and shutters. In time, Cushing was joined in the business by his sons David Jr. and Solon, who kept the store in the family into the twentieth century.