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The Roscoe Phelps diary is a bound manuscript entitled "Anecdotes of the Year 1900" written by Washington and Lee University student Richard Roscoe Phelps (Class of 1902). Phelps reports on life as an undergraduate student touching on courtship, recreation, hazing, off-campus boarding and regional travel and exploration of such places in Rockbridge County Virginia as House Mountain and "Lover's Leap". Other events covered include the vandalizing of "Old George", the George Washington statue atop Washington Hall on W&L's campus, on Washington's birthday; christening a new boat for the crew team, construction of the grandiose and doomed DeHart Hotel in Lexington; the tenure of W&L president William Lyne Wilson; a local opera house fire; and a detailed description of the Biltmore Estate in Asheville, North Carolina. This collection also includes a copy of The History of Rockbridge County Virginia, by author Oren Morton which descended in the family of the donor. The book is inscribed by Samual M. Dunlap.

This collection consists of a souvenir calendar of Lexington, Va. for 1901. It includes images of Washington and Lee, Virginia Military Institute, and Recumbant Lee statue by Edward V. Valentine.

188 photostats of letter from Thomas "Stonewall" Jackson from various places in the United States, Mexico, and at sea to his sister Laura Jackson Arnold and niece.

This broadside by the Valley Railroad titled 'To the People of Rockbridge' outlines funding for the railroad to be built through the county. It asks the people of Rockbridge to help finance the railroad by buying stock in it. It makes the argument that the county's prosperity depends on the railroad. It says students at Washington and Lee University and Virginia Military Institute should no longer be expected to walk through the mire to travel to and from their families and that the railroad will add value to property and give the county access to trade markets.