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The collection is equally divided between letters written by members of the Otis family and letters and documents relating to them. The earlist item is a 17th century marriage settlement and there are a few letters written in the 19th century. The bulk of the collection, however is from the second half of the 18th century. The largest number of letters were written by Joseph Otis (1726-1810), his brother Samuel Allyne Otis (1740-1814), and their father, James Otis (1702-1778). There are a few letters from and relating to Joseph's more famous brother, James Otis of Boston (1725-1783) who was one of the more colorful and incendiary figures in pre-revolutionary New England. Also, letters and documents of George Washington, John Bradford, Josiah Quincy, and Edward Wigglesworth. The letters deal largely with legal and business matters, but there is some comment on events of contemporary interest.

Personal, business, and legal letters; manuscripts including prose, poetry, and diaries; and documents including deeds, receipts, invoices, and account books. The 18th century materials focus on the personal and business correspondence of Calvin, Jotham, and Martin Gay, sons of Ebenezer Gay who were engaged in shipping between New England and the Maritime Provinces. There are occasional letters of Jotham and Martin referring to the American Revolution. The Otis family correspondence of the 18th century, likewise, is of a purely routine and personal nature. There are only four letters of Col. James Otis, and only two of his son, James. Gay and Otis family interests intertwine during the 19th century with the marriage of Mary Allyne Otis to Ebenezer Gay, who are among the chief correspondents of this century, along with their children including Sidney Howard Gay and Winckworth Allan Gay. The Otis correspondence centers around business, real estate, and personal interests of Mary A. Otis Gay's brothers John, Joseph, and William Otis.