American educator who, as president of Mount Holyoke College from 1901 to 1937, greatly improved the school's resources, status, and standards.

Woolley graduated in 1884 from Wheaton Seminary (now College), Norton, Massachusetts, after which she taught at the seminary (1885–86, 1887–90). A European trip in 1890 stimulated her ambition for further education, and in 1891 she was the first woman admitted to Brown University, Providence, Rhode Island. Woolley was one of the first two women to graduate, in 1894, and she remained an additional year to earn a master's degree in history. She then taught biblical history and literature at Wellesley (Massachusetts) College (1895–1900).

Early in 1900 Woolley was chosen to succeed Elizabeth Storrs Mead as president of Mount Holyoke College, South Hadley, Massachusetts, and after a tour of Great Britain, during which she studied women's educational practices and problems, she assumed her new office in January 1901. Under her leadership the academic standards of the college were raised, salaries and benefits improved, and elective courses multiplied. The graduate program also was greatly expanded. The physical plant of the college grew by 16 major buildings during Woolley's 36-year tenure, and the endowment increased 10-fold, to nearly $5 million.

The two principal causes outside Mount Holyoke that attracted Woolley's support were woman suffrage and peace. She retired as president of Mount Holyoke in 1937. Because of her strong disagreement with the trustees' choice of a man to succeed her, she never returned to the campus. Woolley remained active in various organizations, notably the National Woman's Party, until her death.