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This collection contains correspondence addressed to James and Azubah Dalrymple of Framingham and Marlborough, Massachusetts, as well as 2 letters addressed to their son William. William Dalrymple wrote 14 letters to his parents while seeking work in Boston and Montréal and wrote about his impressions of Canada and the residents of Québec. Additional material includes personal correspondence from family friends and from the Dalrymples' daughter Ann.

This collection contains 17 letters addressed to James and Azubah Dalrymple of Framingham and Marlborough, Massachusetts; 2 to their son William; and 1 to their son John.

William Dalrymple wrote 14 letters to his parents while living in Boston, Massachusetts, and Montréal, Québec, between 1805 and 1811. He worked a number of jobs and spent some time as a shoemaker's assistant in Providence, Rhode Island (September 17, 1805). While working at a store in Boston, he commented on the prices of hardware and requested that his parents send him a pair of shoes, to be made by his brother John (March 24, 1808); later that year, he traveled to New York and shared his impressions of the city (June 13, 1808). In May 1809, he moved to Montréal, where he discussed Canada's ties to European culture (June 27, 1809) and reported his opinion of local residents (September 28, 1809). His letter of April 3, 1810, to his brother John encourages John to take advantage of local schools (April 3, 1810). William responded to the death of his young sister Sally in his letter of May 8, 1810, and wrote his final letter home on May 7, 1811.

William Dalrymple received two letters from George Rich, who provided his opinion on the economic climate of Baltimore (December 24, 1806) and awaited the arrival of the United States schooner Revenge, which would bring news of international tensions between the United States, Great Britain, and France (October 26, 1807). His later letter also refers to William's efforts to become a playwright. James and Azubah Dalrymple also received letters from their daughter Ann, who wrote about a family in Cambridge (June 17, 1823); Jabez Green, a friend, who requested news of his son Benjamin in New York City and mentioned the construction of a canal between Albany and Lake Erie (September 17, 1824); and Timothy Woodbridge, a Presbyterian minister from Austerlitz, New York, who reported the death of James Dalrymple, Jr., on August 28, 1835 (September 2, 1835).