In 1784, Robert Macaulay (1744-1800) was among the founders of the settlement of Cataraqui that became the city of Kingston, Ontario. He and his family acquired wealth and influence as merchants and landowners, publishers and bureaucrats. In particular, his son, the Honourable John A. Macaulay (1792-1857), wielded considerable influence in politics and the government of the province. The family acquired houses and furnishings that reflected their prominent status.

Robert Macaulay and Ann Kirby (1770-1850) were married at Crown Point, New York, in 1791. As the date of manufacture for this elegant, Neo-Classic sugar vase coincides with the date of their marriage, it is believed to have been a wedding gift.

Robert Macaulay apparently met his future wife during a visit to New York State in 1786 to seek compensation for losses incurred during the American Revolution. He returned to marry her in February 1791. They rode to his home in Kingston on horseback across the ice of Lake Ontario.