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A leading citizen and reformer in Chicago, Woolley was born on June 14, 1848 in Toledo, Ohio to active abolitionists, Marcellus Harris and Harriet M. Parker. She grew up in Coldwater, Michigan and attended Coldwater Female Seminary. She married Dr. J.H. Woolley, a dentist, in 1868. After they moved to Chicago, Woolley became very active in the social and cultural life of the city. She joined the Chicago Woman’s Club, was its president for a time, and opened up its membership to blacks. She achieved this by working with her friend Fannie Barrier Williams, a black Unitarian lay woman. Woolley joined the editorial staff of the Unitarian publication, Unity, in 1884 and continued to help in some capacity until her death in 1918. She published articles in the Christian Register, and several books, including Love and Theology. She became a director of the Western Unitarian Conference (WUC), but she was alienated by the divisive politics involved. She was also in demand as a lecturer on such issues as woman suffrage.
In 1894 she was ordained to the Unitarian ministry, and served for three years in Geneva, Illinois, and then for two more years in Chicago at the North Side Church, where she tried to evoke a social conscience in her parishioners. She was closely associated with Jenkin Lloyd Jones who preached her ordination sermon, and she frequently supplied his pulpit at All Souls. Always concerned with issues of racism and human rights, Woolley and her husband moved to the black neighborhood on Chicago’s South Side in 1904. Here she established the Frederick Douglas Center to provide programs and services that would open greater opportunities for blacks and foster greater cooperation between the races. She devoted many years to this community ministry, where she lived and worked. At first she hoped it would be a type of settlement house, but it evolved into a meeting place for middle-class blacks and whites to find common ground, and so concerts and teas, a poetry series and lectures on topics such as vegetarianism became the more typical programs. Although she was criticized for not helping those with the greatest needs, Woolley did much for breaking down racial barriers.