The correspondence is divided into three groups. The first group covers the years 1840-1981. It includes letters written by John H. Timberlake to his cousin and future wife Etta Gertrude Bowe while he was teaching at Southwood Academy in Talladega, Alabama, and later while he was serving with the 4th Virginia Cavalry at Culpeper Courthouse, Brandy Station, Yorktown, Richmond, Hanover County, Martinsburg, and Spotsylvania Courthouse. Of particular note is a letter, dated 4 July 1862, in which he mentions his action as an escort and guide for General Stonewall Jackson to Cold Harbor. There are transcriptions for these letters which cover the years 1858 to 1863. Also included in this group are letters of sympathy written upon the death of John H. Timberlake (1900) and Etta Gertrude Timberlake (1911). There are also numerous letters written to Carrie Crenshaw Timberlake from friends in Germany and France. Much of the post-1900 correspondence is between Gertrude and Carrie while the latter was teaching at Lewisburg Female Institute, and contain information regarding Gertrude's activities in the United Daughters of the Confederacy, including conventions she atttended in Norfolk and San Francisco, as well as her visit to the Lewis and Clark Exposition in Portland, Oregon in 1905. There are also descriptions of trips by Gertrude to Jamestown and Nashville, Tennessee. There are numerous letters to Carrie concerning her interest in genealogy from fellow researchers, and also relating to her finances and investments. Also included in this group are letters written by Donald C. Timberlake (1915-2007) to his wife Ethel Lee (Culley) Timberlake (1916-2009), while he was serving in the Army in Italy during World War II.

The second group of letters covers the years 1871 to 1911, and includes many letters from her parents to Carrie while she was attending Wesleyan Female Institute in Staunton, and later teaching in Botetourt County, Virginia. The correspondence from 1896-1897 is between them while Carrie was studying overseas in Hannover, Germany and Paris, France. There are also letters written by John H. Timberlake in 1899 while he was in Hot Springs, Virginia, and Asheville, North Carolina for health reasons. The post-1900 letters are mainly between Gertrude and Carrie while the latter was teaching in Lewisburg and the Stonewall Jackson Institute in Abingdon, Virginia, as well as when she was on trips to England and Scotland and also out west at Yellowstone. There are transcriptions for some of these letters.

The third group of letters covers the years 1896 to 1898 and 1901 to 1903. It includes letters written by Carrie to her parents while she was studying in Germany, as well as visiting Italy and France. She also kept two letterbooks containing the text of these letters. These two volumes can be found in the Subject Files. The 1901-1903 correspondence are letters written to Ruby Franklin Beach (1884-1948) prior to her marriage to Maury Cullen Timberlake (1878-1935).

The subject files contain a variety of materials relating to the activities of the Timberlake family. There is information relating to the Army service of Donald C. Timberlake during World War II, autograph albums, historical information on Atlee, Atlee's Station, Cool Spring Baptist Church, and Washington-Henry Academy, Bible records, books, and botanical samples collected by Carrie C. Timberlake, and clippings. There are Civil War papers of John H. Timberlake, including a discharge, furlough, oath, and ladies' pass for Gertrude Bowe. The subject files also contain a large amount of material relating to Carrie's extensive travel, including cruise books, menus, passenger lists, programs and itineraries, tickets and passes, tourist brochures and guide books, and a travel journal. There are also deeds, diplomas, estate papers, genealogical notes on the Anderson, Bowe, Carr, Chiles, Clopton, Crenshaw, Dabney, Davis, Garland, Graves, Hill, Meredith, Shelton, Timberlake, and Tinsley families, letters of recommendation, obituaries, plats and surveys, photographs, poetry, postcards, recipe books, and scrapbooks. Finally, there is information relating to the development of the Timberlake home "Rutland" into a mixed-use residential community, and also information on the family's investments and rental properties, and also tax records. Of note are four volumes of tax books (1841, 1844, 1845, 1847) kept by Archibald Burnett Timberlake (1809-1863).