Correspondence includes letters, telegrams, notes, invitations, cards, and publications written by or sent to Woolley, primarily dating from 1899-1947. These documents chiefly concern her professional activities, although the series also includes several letters that she wrote to her grandparents in the 1870s. There are letters and programs reflecting her involvement with the Institute of Pacific Relations Conferences in Hawaii (1925 and 1927), the Conference on Reduction and Limitation of Armaments in Geneva, Switzerland (1932) and the International Federation of University Women's 23rd Council Meeting (1938). Of particular note in these materials are letters from representatives of peace organizations including the Women's International League for Peace and Freedom and the Conference on the Cause and Cure of War. Other correspondence is with Mount Holyoke College alumnae and members of alumnae clubs, representatives of academic institutions, and many organizations, including The American Association of University Women, the League of Nations Association, and the League of Women Voters. These letters most often concern speeches and articles that Woolley presented to various groups. Other correspondence concerns individuals whom she invited to speak at Mount Holyoke College. The correspondents includes one or more letters by Herbert Hoover, Eleanor Roosevelt, Franklin D. Roosevelt, M. Carey Thomas, Jane Addams, Frances Perkins, and Virginia Woolf as well as letters from many Mount Holyoke College trustees, faculty, staff and alumnae.

Speeches and Articles consist of published works by Woolley as well as unpublished typescripts, manuscripts, and notes. Most documents dating from her tenure as president of Mount Holyoke College (1901-1937). The speeches, which comprise most of the series, were most often given at meetings of professional, religious, or civic organizations and at commencement or convocation ceremonies at various institutions. They include the text of a number of that Woolley presented to Mount Holyoke College students as well as scripts for radio broadcasts that she made while attending the Conference on Reduction and Limitation of Armaments in Geneva, Switzerland in 1932. Her articles were published in magazines, journals, and books, including , , , and the . Frequent topics of her speeches and article include the education of women, international relations, world peace, and the role of spirituality in politics.

Consists of bibliographies of Woolley's writings and copies of her published essays, articles, and speeches, primarily dating from 1901-1938. Many of these documents appeared in magazines, journals and newspapers including , the , the , the , the , and the . Topics of these writings include world peace, the education of women, and the college woman in society. Included in these writings are Woolley's M.A. thesis about the history of the colonial post office (1894) and her inaugural address as President of Mount Holyoke College. There are also two anthologies containing essays by Woolley: a book for young adults entitled (1931) and (1935), an anthology of essays advocating disarmament.

Consists primarily of drafts for an autobiography that Woolley began preparing after her retirement from Mount Holyoke College. Consists of drafts, notes, and memoranda relating to her life and includes information about her family, education, experiences at Mount Holyoke, and participation in the Conference on Reduction and Limitation of Armaments in 1932. This material also includes a draft of an essay entitled that Woolley wrote during her childhood.

Consists of a variety of notebooks containing brief notes relating to Woolley's daily activities. One volume contains , a daily journal of her observations at the Conference on Reduction and Limitation of Armaments at Geneva as it appeared in the in April 1932. Some notebooks also include addresses of friends and colleagues.

Consists of notebooks, minutes, schedules, reports, notebooks, correspondence, publications, petitions, and programs reflecting Woolley's membership or participation in several major commissions and conferences. These materials concern the Foreign Missions Conference of North America Educational Commission to China, which studied Christian higher education in that country (1921), two Institute of Pacific Relations meetings in Honolulu, Hawaii (1925, 1927), the Conference on Reduction and Limitation of Armaments in Geneva, Switzerland (1932), and the International Federation of University Women's 23rd Council Meeting in London (1938). Include in the Geneva conference materials are many letters and petitions from individuals writing in support of world peace and a volume of sketches of delegates by Oscar Lazar.

Consists of seven scrapbooks containing newspaper and magazine articles, programs, and postcards, dating from 1901-1941. Most of the material in these volumes relates to Mount Holyoke College and Woolley's position as President of that school. Many of the articles in these scrapbooks are from the Springfield, Massachusetts , the Boston , the and the . A scrapbook devoted to the 1932 Conference on Reduction and Limitation of Armaments contains newspaper articles about that meeting, several articles written by Woolley, and a copy of a joint address on that she prepared with Frederic William Wile.

Consists of surveys, questionnaires, correspondence, publications, a notebook, and notes about the faculty, staff, students, curriculum, library collections, finances, buildings and grounds between 1903-1919. Statistical surveys and questionnaires completed by Woolley and Office of the President staff were prepared for the United States Bureau of Education and Bureau of the Census, the National Association of State Universities, the , and the . These documents include a detailed questionnaire about from 1916 that describes the furnishings, regulations, and maids and other support staff of residence halls as well as the foods typically served to students. A notebook of dating from circa 1907-circa 1912 includes information about the living arrangements and salaries of faculty and staff, the grading system, the graduate work, and scholarships and fellowships. Some statistics from 1904 concern secret societies at the school.

Contains Committee of Inauguration minutes, guest lists, invitations, correspondence, programs, sheet music, tickets, and newspaper clippings relating to the inauguration ceremony for Woolley, who officially became President of Mount Holyoke College in May, 1901.

Consist of a copy of Woolley's birth certificate, a smallpox vaccination record for her, the diplomatic passport issued to her when she served as a delegate to the Conference on Reduction and Limitation of Armaments in 1932, and a copy of her will.

Contains lists, notes, correspondence, certificates, citations, tributes, badges, pins, medals, coins, and ribbons chiefly relating to honors and awards bestowed on Woolley. Includes citations for the many honorary degrees that she received and a medal presented to her as a delegate to the Conference on Reduction and Limitation of Armaments in 1932. Also includes a (1939, 1945) and a volume of tributes presented to Woolley by Mount Holyoke faculty members upon her retirement as President of the College in 1937.

Includes announcements, programs, lists, notes, a calendar, greeting cards, a diploma, membership certificates, guest books, and copies of poems and prayers collected by Woolley. Some materials relate to her participation in the Conference on Reduction and Limitation of Armaments held in Geneva, Switzerland in 1932. These items include a collection of signatures of delegates to the conference, postcards of buildings in Geneva, a menu for a dinner, and a booklet describing the S.S. , the ship on which she sailed to Europe. The guest books in the collection record information about visitors to Mount Holyoke College during Woolley's tenure as President (1901-1937). Also included in the series is information about Woolley's dogs, including notes that she wrote to them while attending the conference in Geneva.

These volumes consist of several Bibles, books relating to Mount Holyoke College, and other books owned by Woolley. The Bibles include one . A copy of the Whittier Birthday Book (1881) contains the names of several individuals and is inscribed . Another book entitled (1909) is a book filled with ghost shadows, or signatures of Woolley's friends folded and pressed so that they create unique shapes.

Contains published biographical sketches, newspaper and magazine articles, essays, obituaries and tributes concerning Woolley and her accomplishments. Includes articles entitled (, October 1903), (, March 1931), (, February 1932), and (, June 1937).

Consists of several copies of a 78rpm sound recording of , a chapel talk given by Woolley on September 24, 1920 that was recorded and distributed to raise funds for a Mount Holyoke College endowment campaign. Audio cassette and a tape of this recording are also part of the series. There is a recording from March 23, 1937 labeled that may contain an interview of or about Woolley by Marion Barbour (Class of 1920) and an undated silver-coated recording of an address that Woolley gave to Mount Holyoke alumnae clubs.

Chiefly consists of formal portraits, snapshots and glass plate negatives dating from about 1864-1947 that show Woolley alone or with relatives, friends, colleagues, Mount Holyoke students, distinguished visitors to the College, or her beloved pet dogs. Some photographs are reproductions of paintings and drawings of her. Includes photographs of people, buildings and scenes taken during a trip to in 1921, when Woolley was a member of a commission studying Christian education in China, as well as photographs of her at the Conference on Reduction and Limitation of Armaments (1932) and other meetings. Also includes photographs of Woolley's parents and siblings, an album dating from circa 1845-circa 1870s containing photographs of unidentified individuals (probably relatives), and another album that primarily consists of photographs of Woolley's dogs.

Consists of two card indexes, 1901-1947. One is an alphabetical list of the names of correspondents represented by letters in the collection (Series 1). The other is an alphabetical list of the titles of Woolley's speeches and articles that are part of these papers (Series 2). The latter index provides the number assigned to each work by which the speeches and articles are filed.

Contains oversize items described as part of other series in the collection. The container list description of these items includes an indication that they are shelved in Folio.