This pocket diary of Charles Edward Bailey contains entries dated 1 January-17 December 1860 (with gaps) describing farm work, including work on a henhouse and packing and delivering eggs; picking up and delivering goods; tending a store; frequent attendance at church and prayer meetings; trips into Boston; and news of family members.

The three pocket diaries of Eudora (Turner) Bailey, 1865 and 1880-1881, describe her daily activities; activities of Turner and Bailey family members, including her husband Charles Edward Bailey and their children; attendance at church services, sewing circles, temperance meetings, etc.; social calls; her health; and the weather. Entries in the 1865 diary describe a visit from her brother William Francis Turner on furlough, his bout with measles, the end of the Civil War, and the assassination of Abraham Lincoln. Many pages in this diary are blank. The 1880 and 1881 diaries have more and fuller entries related to her children; household work, such as sewing, washing, and ironing; regular attendance at the First Baptist Church in North Scituate; and other subjects. A few entries in 1881 discuss the assassination of James Garfield. Eudora also frequently mentions Charles's sister Sarah Tilden Bailey (1824-1914), who lived with them, and someone named Dora, who helped with housework; Dora may have been a younger family member or a servant. All three volumes include accounts.

The diaries of Josephine Maria (Litchfield) Bailey include four pocket diaries kept when she was a teenager and young woman, 1880, 1883, and 1889-1890. Entries describe activities with friends and with Litchfield and Bailey family members; attendance at school, church, and temperance meetings; housework with her mother Rebecca (Cudworth) Litchfield; courtship and marriage to Henry Turner Bailey; the building of their home called Trustworth; her first pregnancy; and the weather. Bailey was very active in her church, the First Baptist Church of North Scituate, and frequently mentions Rev. Thomas Richard Peede.

The other three diaries date from later in Bailey's life and contain entries from 1935 and 1941-1942. These diaries describe her daily activities, primarily with her children and their spouses and children, including Elisabeth Bailey, Lawrence H. Bailey, Margaret (Bailey) Miles, and Max D. Miles; activities of her son Gilbert, who had a developmental disability; social calls; sewing; listening to the radio; frequent injections, probably to treat her pernicious anemia; home improvements; the sale of her mother's house; and the weather. Included are only a few references to World War II and one page at the end of 1942 recording blackouts and air raid alerts. Elisabeth Bailey added a few entries about her mother's final illness and death in December 1942.

The two pocket diaries of Henry Turner Bailey were primarily kept while he was a student at the Massachusetts Normal Art School in Boston, 1884-1885. Entries describe his daily activities; classes, examinations, and work on various assignments; dates with his future wife Josephine "Jo" Litchfield, his love for her, and her decision to join his church, the First Baptist Church in North Scituate; attendance at church, Sunday School, and prayer meetings; teachers' meetings; books he read; and a bout with measles from December 1884-January 1885. Beginning in September 1885, Bailey worked as supervisor of drawing in Lowell, Massachusetts. Entries describe visits to schools, meetings with teachers, and lesson planning. Both volumes include miscellaneous cash accounts.

The thirteen diaries of Elisabeth Bailey, 1943-1955, describe her daily activities and those of other Bailey family members, especially her aunt Sarah Tilden (Bailey) Brown and her brother Gilbert Turner Bailey, who both lived with her. Gilbert had a developmental disability. Other people mentioned include her brother Lawrence H. Bailey, sister Margaret (Bailey) Miles, brother-in-law Max D. Miles, niece Josephine Miles (later Schuman), and other nieces and nephews, as well as many friends.

The diaries describe home improvements and repairs; gardening, cooking, and sewing; listening to the radio, going to the movies, and (beginning in 1950) watching television; social calls and local news; services at St. Stephen's Church in Cohasset, Massachusetts; meetings of an unspecified church guild (possibly a women's guild), missionary meetings, and choir rehearsals; the flu epidemic of 1943-1944 and other health matters; the weather, including the Great Atlantic Hurricane of September 1944; post-World War II labor activity; and other subjects. Entries written during World War II reference war news, sightings of soldiers and blimps, occasional blackouts, and rationing. All of the volumes also contain miscellaneous memoranda, mostly lists of Christmas gifts and cards. The 1955 diary includes an entry about Elisabeth Bailey's death written by Margaret Miles.