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This collection contains letters, diaries, sketches, publications and other material created and collected by Dennis Loy, a gay artist who exhibited works in the Chicago area and New York City. Most of the letters were written to Loy by his cousin, American writer and journalist P.J. O'Rourke, and cover such topics as poetry, politics, drugs, art, and gay culture in the 1980s.

Diaries, 1941 and 1962, of Jennie Gore, a teacher from Wartrace, Tennessee. Includes brief entries about her daily life, including work matters, people with which she met, and her daily activities. The 1941 diary also includes information about a road trip through Canada and the East Coast of the United States.

Papers, 1800-1901, of and relating to John Hipkins and John Hipkins Bernard (mostly accounts); of and relating to members of the Hipkins, Bernard and Robb families; and relating to the Hipkins-Bernard-Robb home "Rose Hill," Caroline County, Va. (later renamed "Gay Mont") and to Bernard's lands in Alabama, Texas and Arkansas. Includes diaries, correspondence, poems, accounts and account books of women (Elizabeth Hipkins, Jane Gay Robertson Bernard, and Helen Struan Bernard Robb); and legal documents and letters of John Taylor of Caroline. Of special interest are the diaries of Eugenia D. Robb while serving with the American Red Cross in Germany and Japan during and after World War II (1999.56A).

Diary, 1914, of the Youngblood family as they traveled from Red Deer Lake, Alberta, Canada, to Sandpoint, Idaho. The journey was taken in a horse drawn wagon and took from June to September of 1914. Topics include campsites, people that they met, goods purchased, and traveling through lands populated by Native Americans.