Woolley retired in 1937 at the age of 74. The appointment of Roswell Gray Ham to succeed her was a bitter blow to opportunities for women to advance through higher education. She, members of the faculty, members of the AAUW and members of the alumnae group fought back strenuously. The vote at the June 6, 1936 Board meeting just achieved the required majority despite eloquent pleas from trustee Frances Perkins (a Mount Holyoke alumna and Secretary of Labor), Woolley and members of the faculty. After Ham was appointed, some alumnae attempted to rouse sufficient opposition to convince Ham to refuse the appointment but official Mount Holyoke closed ranks and the opposition was defeated. Woolley and her allies did have the "last word" at the college's centennial celebration in May 1937 (a month before Ham took office). He was not invited to attend and many of the speeches decried the actions of the Board of Trustees. After her retirement, Woolley never visited the Mount Holyoke campus again. She moved to the Marks family home in Westport, NY and lived there with Marks until her death in 1947.