One of nine children, Jane Redpath Drummond came from a privileged household, where watercolour painting would have been an acceptable and even encouraged feminine pursuit. Women in Drummond’s position often received training in the medium at home.

When Drummond was born, her father was manager of the Commercial Bank of Canada in Ottawa, having moved from the branch in Kingston. A year later, he became manager of the Bank of Montreal in Ottawa. Drummond’s mother, Margaret Sinclair, was the niece and adopted daughter of John Mowat and raised in Kingston as a sister to Sir Oliver Mowat, who later became one of the Fathers of Confederation. Jane Redpath Drummond painted watercolours at Ottawa, and in 1891 exhibited in the Spring Exhibition of the Art Association of Montreal.

By 1900, Drummond appears to have moved to her mother’s hometown Kingston. Over the next two decades, she produced a considerable body of small watercolour landscapes in and around the city: homes, the waterfront, and historical landmarks such as the Martello Towers, City Hall, Queen’s University, Cataraqui Bridge and the “Simcoe House” (once on Queen Street, it was mistakenly believed to have been the first meeting place of the Executive Council of Upper Canada). In doing so, she was part of a collaborative network of women artists in Kingston in the late nineteenth and early twentieth centuries, who learned from each other, painted together on informal outings, and likely shared print images for the practice of their art. Drummond and fellow artists Ella Fraser, Jane Dainty and Ethel Wood often painted the same views, revealing subtle variations of personal style.