This series consists of typed transcripts of Bailie's journals, which she kept faithfully from 1886 to 1959. They are highly personal. She described them as "a picture of my life, at home and outside. Only to my journals did I reveal my struggles."

The journals also reveal Bailie's social, political and cultural milieu. They document her early experimentation with anarchism; vegetarianism; and companionate marriage and her relationship with William Bailie, as she copes with his marital infidelity, six children from an earlier marriage, and financial difficulties. They also reveal her grief at the time of her young son's death and mark the difficulties she encounters raising her daughter, Helena. The struggles of daily life during World War I and II are also noted, as she includes grocery lists and records the price increases and limited availability of food items.

Entries from the late 1920s document the Daughters of the American Revolution, "Red Menace" scare, and "blacklist" controversies. The journal entries from this time reveal personal difficulties and doubts which are not apparent in Helen's public statements.

Some of the later entries consist solely of letters exchanged between Helen and her daughter Helena, while Helena was an instructor at Wilberforce University in Ohio, They are revealing about Helena's work in the field of sociology, and the relationship between mother and daughter.

Included in this series are photocopies of six photographs (1895-96) of Bailie with friends, particularly Helena Born. The original photographs are located at the Tamiment Library in New York City.

This series is divided into three subseries: The Daughters of the American Revolution and the Red Scare, Disarmament and The Teachers Oath.

The bulk of Bailie's professional papers relate to the DAR "blacklist" controversy and the "Red Scare" of the mid to late 1920s. Because the two issues are intertwined, they have been combined into one subseries. This subseries includes correspondence, articles, clippings, pamphlets, press releases, DAR documents and records of the charges against Bailie, her protest writings, and information about other organizations involved. The articles and pamphlets (1925-29) reflect both sides of the controversy and contain articles by Carrie Chapman Catt.

The correspondence in this subseries, arranged alphabetically by sender, is both personal and professional, and is primarily a record of Bailie's fight against the DAR "blacklists" and policies during the mid to late 1920s. It also contains public and private letters received by Bailie that both supported and protested her position. There are also third party letters which were most likely forwarded to Bailie. Noted correspondents include Grace G. Brosseau (President General of National DAR, 1925-28) and Florence Luscomb (1928).

The Daughters of the American Revolution and the Red Scare subseries contains publications from a number of organizations involved in this controversy, both those on the "blacklist" and patriotic organizations in support of the DAR. They include American Peace Society, Better America Federation, American Vigilant Intelligence Federation, Key Men Of America, Lusk Committee, Massachusetts Public Interest League, National Defense Life Insurance Company, National Save Our Schools Committee, and Women's International League for Peace and Freedom.

The second subseries records Bailie's interest in a controversy regarding naval propagandist, William B. Shearer and naval disarmament (1927-30). Shearer who was investigated by the Senate was hired by shipbuilding companies to attend the Geneva armament conference, ostensibly to argue against limitation of naval armament. It includes articles, correspondence and published materials.

The remainder of the series relates to Helen's fight for repeal of the Teacher's Loyalty Oath law in Massachusetts from 1935 to 1937. It consists of clippings, pamphlets and correspondence. Among names included are Jeannette Marks (Professor at Mount Holyoke College) and Lucille B. Milner (Secretary of American Civil Liberties Union).

This series consists of speeches (1928, n.d.); Darling Daughter: A Satirical Novel (1956); "Fata Morgana," a short story (1939); and "Buttermilk," a play (n.d.) by Bailie. It also includes Whitman's Ideal Democracy And Other Writings by Helena Born, edited by Helen Tufts Bailie (1902)