This small collection consists mostly of correspondence from members of the Eldred family sent to Wilfred Eldred while at school on the East Coast. There is also a diary kept by Wilfred while a student at Washington and Lee in 1908, and letters from Wilfred to the family twenty years later. Winifred and Edith, Wilfred's sisters, and his father William Eldred wrote long letters to Wilfred updating him on the family's activities and on life in San Diego. The family is active in the developing city (especially in Point Loma) during important years in San Diego's history.

Correspondence is especially rich during the 1912-1916 run. Winifred's letters to her brother usually concern her teaching responsibilities at Washington School in San Diego, questions surrounding her future education, and give vivid descriptions of her experiences in the developing city, especially Point Loma.  In 1915 she attends UC Berkeley while Wilfred is at Stanford, and the siblings see each other frequently; she writes regarding finances and shared trips home.

William writes to Wilfred of troubles in the real estate business due to local wildfires in 1913, but details later expansion as San Diego prepares for the Panama-California Exposition of 1915 (though the Exposition, "a sickening nuisance," is not always smiled upon by the family).

Edith, a student at San Diego High School, is editor of the school yearbook The Russ and a champion debater on the school team. Though Edith's letters deal with typical teenage concerns like clothes, theater performances, and friendships, she also refers to mature topics like women's suffrage and immigration policy. Mother Eliza writes infrequently, but William's letters mention her activities often, including her work as director of the Point Loma Club in 1913.

Later correspondence from Wilfred to his father during the late 1920s and early 1930s refer to national economic problems during the Depression. A folder of incoming correspondence to William from 1908-1933 includes letters from authors and publishers from his time as a book reviewer in Norfolk, Virginia.

Several notable personalities in San Diego history interacted with the family. Winifred was close friends with socialite Jessie Ball and her sister Isabel; Jessie went on to marry into the famed DuPont family and the two remained close throughout their lives. William was devoted to his cottage garden, and Edith notes in a 1913 letter that their father has brought home noted botanist Kate Sessions for gardening advice. The "socialist singer" Miss O'Byrne, who apparently settled on a ranch near San Ysidro after touring in Southern California, is also acquainted with the family.