The Thompson Family papers include the correspondence, manuscripts, and financial papers of John P. Thompson, Sr. (dates unknown), a Confederate officer and Democratic politician, his wife Neilia Cave Thompson (dates unknown), their son John P. Thompson, Jr. (1967-1945), and his wife Florence Kemper Thompson (1859-1944), daughter of Confederate general and Virginia governor James Lawson Kemper.

The correspondence series, dating from 1862 to 1918, consists of personal and financial correspondence. John P. Thompson, Sr., a native of Owensboro, Kentucky, joined the Confederate army in 1861 and was commissioned a Captain commanding Company G, 1st Kentucky Cavalry. He went with his regiment to Manassas Junction, Virginia to join Confederate forces there under Joseph E. Johnston. When Union troops under Brigadier General Ulysses S. Grant seized Paducah, Kentucky, to counter a Confederate thrust into the then-neutral Blue Grass state, Thompson and his company petitioned Confederate president Jefferson Davis to let them return to defend their native state. Davis refused their petition, claiming that Confederate forces in Virginia were too small to allow a further reduction of strength. After a year's service in the Eastern theater, Thompson was promoted to Major and sent home to Kentucky in 1863 to recruit new members for the regiment. He was captured behind enemy lines at Owensboro and sentenced to be shot as a spy, but Confederate authorities intervened and got the sentence reduced to imprisonment at Johnson's Island, Sanduscky, Ohio, where he remained until the close of the war. While in prison he corresponded with Neilia Cave of Orange, Virginia, a girl he had met while stationed there with his regiment. Thompson returned to Orange, and married Neilia; their son, also named John P. Thompson, was born in 1867. The elder Thompson returned to Kentucky to engage in politics on the Democratic side. His letters to his wife discuss his political activities. He seems to have passed away in the later 1870's.

Most of the correspondence between 1870 and 1918 concerns the younger John P. Thompson, his mother, and his wife, Florence Kemper Thompson. The letters trace Thompson's early wide-ranging attempts to establish himself in business and his search for a bride in places ranging from San Francisco to New York City. In 1899 Thompson married Florence Kemper, owner of "Walnut Hills" in Orange County, Virginia. She had inherited this small estate of her father, Confederate general and Virginia governor James L. Kemper, upon his death in 1895. The couple remained childless. The remaining correspondence concerns Thompson's efforts to change "Walnut Hills" from a simple home into a summer resort and develop the farming business by expanding into raising bulls and steers. Much of the correspondence is personal correspondence between the Thompsons and the widowed Mrs. Thompson, who had moved with Leslie H. Gray to Brooklyn, New York. These letters describe and contrast city life in New York at the turn of the century, including famous city personages such as Frederick Dent Grant, eldest son of Ulysses S. Grant, with Southern rural society with its traditions and memories of the Lost Cause. The Thompsons sold "Walnut Hills" around 1930. Florence Thomspon died in 1944, her husband died a year later.

The manuscript series dating from 1884 to 1911 includes several memorandum books kept by the Thompsons recording letters mailed and attendance at local dances. There are some recollections of Neilia Cave Thompson about life in Civil War Virginia, several unsigned stories, and a few humorous political anecdotes.

The financial papers, spanning the years 1860 to 1918, regard the younger Thompson's business transactions in attempting to develop his farm. Other financial papers concern "Walnut Hills," including guest lists and typewritten drafts of descriptive brochures, and Thompson's bulls.

The printed material series, from 1898 to 1928, consists mainly of advertisements for farm machinery and fashions. There are several medical periodicals, a play program, and postcards and printed brochures about "Walnut Hills." Several unidentified photographs are located at the end of the collection.