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Letters written to Gay from political and literary contemporaries such as Horace Greeley, Charles Sumner, and William Bryant; reports in letter form from his reporters at the front during the Civil War; and personal correspondence including many letters from his wife, Elizabeth Neall Gay. Letters written to Mrs. Gay from family friends and business associates including many from her husband. Correspondence of other members of the Gay family including Walter Gay, Sarah Gay, and Allan Gay. Diaries, notebooks, and journals of Sydney Howard Gay.

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.

Correspondence, manuscripts, original drawings and sketches, and memorabilia of Reinhart. Of the 247 letters in the collection, a number are from E.A. Abbey, William Dean Howells, and Henry James. There are eight original drawings and sketches and two sketchbooks, as well as numerous photostats and clippings of his works that appeared in magazines. Also, a group of letters to the artist's son, C. Stanley Reinhart, relating to the disposition of various paintings to galleries and museums throughout the country.