The collection is made up of two sections, correspondence and essays (both arranged alphabetically by author). The bulk of the collection is by George H. Dole, with almost half of his correspondence to his wife Clara Rowell Dole and several letters to his children. Thirty-one of the forty-five school essays were written by George H. Dole. Many of the items, both correspondence and essays, include the use of the Hawaiian language. George and Clara sign some of their letters with their Hawaiian names (George as Heoki and Clara as Kaalala).

George H. Dole was born in 1842 in Punahou, Hawaii; his brother, Sanford B. (Sanford Ballard) Dole, 1844-1926, also born in Hawaii, became President of the Provisional Government of Hawaii in 1893, President of the Hawaiian Republic in 1894, and in 1900 was appointed the first Governor of the Territory of Hawaii. George and Sanford's parents, Daniel and Emily Dole, came to Hawaii from Maine as missionaries in 1841. The Doles first lived in Punahou, where they opened a school for children. Emily Dole died shortly after Sanford's birth and two years later, in 1846, Daniel married Charlotte Close Knapp, a fellow missionary in Hawaii. In 1855 the Dole family moved to the island of Kauai and opened a school in Koloa. George and Sanford attended the Koloa School and in 1864, at the age of 22, George left to travel in America. In 1867, after returning to Hawaii, George married Clara Rowell and began employment on several sugar plantations, including the Koloa, Kealia and the Kapaa plantations. In 1889, George, his wife, and their twelve children (a thirteenth child was born in 1890) moved to Riverside, California. George worked for the Riverside Naval Orange Company and various insurance agencies. In 1900 George invested money in the Minnehaha Oil Company located in Bakersfield, California. George H. Dole died in California in 1912.

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