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This collection consists of two letters from Washington College (now Washington and Lee) student Alexander S. Brown to his sister, dated September 20, 1846 and September 7, 1848. The 1846 letter mentions the Cincinnati military class, in which Washington College students participated in military training conducted by VMI staff. The 1848 letter expresses Brown's dissatisfaction with Washington College and a desire to transfer to another school.

The bulk of the Charles A. Derby papers consists of Derby family correspondence. Approximately twenty-eight letters were written by Charles A. Derby (dated 1844-1862) and cover the period from late boyhood up to his death in battle in 1862. Included are letters (dated 1846-1847) written while he was a cadet at VMI, as well as correspondence dating from his careers as a teacher and Episcopal clergyman. Two items were written during his brief service in the Confederate Army.

This collection consists of two letters. The first letter (dated July 15, 1844) is from Henry T. Lee (VMI Class of 1845 and Daniel L. Powell's uncle) to Cadets Fitzhugh and Keeling, requesting that they treat Powell with kindness. The second letter (dated August 22, 1846) is from Cadet Powell to his mother, and the letter describes guard duty at "Camp Crozet," the purchase of clothing, and family news.

This collection consists of one letter (dated May 14, 1846) from James E. Tyler (VMI Class of 1845) to President James K. Polk. The letter requests a commission in the United States Army or Marine Corps. Tyler mentions recommendations from Francis H. Smith and John T.L. Preston, and states that he was an "inmate" of VMI for two years.

The John M. Cary papers consist of the papers (three items) of Cary, including:

• Appointment to a state cadetship at VMI (July 1845)
• Letter from Cary to VMI Superintendent Francis H. Smith (July 8, 1845)
• Letter of recommendation by VMI Board of Visitors member William H. Terrill, September 29, 1849). Cary had served as a tutor for Terrill's children.

This collection (four items) consists of items dating from John W. Steenbergen's cadetship, including a one volume notebook that contains copied poetry and notes, two essays, and his VMI account book documenting school expenses (1846-1849).

The VMI historical appointment documents collection consists of notices of appointment sent to new cadets at VMI. The documents date from the 1840s into the 1900s. These are typically pre-printed forms on which the name, date, and other details are filled in by hand. They also include a list of supplies needed and information about expenses.

This collection consists of letters and other documents to and from various members of the Moncure Family, who have a long association with VMI. Included is a letter (dated September 19, 1849) from Cadet Thomas J. Moncure (VMI Class of 1853) to his father, William A. Moncure.

The Philip A. Fitzhugh papers consist of papers relating to Fitzhugh, with a bulk dating from his cadetship. The collection includes:

• Six letters from Fitzhugh to his brother that contain references to cadet life (graduation; hazing "plebes"; death of Henry C. Reid, Class of 1846; Washington College students, called "minks")
• Handwritten issue of a cadet newspaper called "The Royal Caroline" (March 21, 1846)
• VMI letter of appointment
• Two grade reports
• Invitation to a Society of Cadets meeting
• Medical school speech
• Letter to Fitzhugh from Henry T. Lee regarding Daniel Lee Powell, VMI Class of 1844
• Student notebook

The Order Books contain official orders and notices concerning the military regulations and operations, as well as the academic administration of the Institute. The definitions of Orders, Special Orders, and Memoranda overlap and vary over time.