Her teacher, Bessie Whitaker, helped her go to the nearest high school in Ithaca by finding her a place to live and work with the family of Cornell professor Robert Chamberlain [See 1910 census "Relatives"].

"At the agricultural college, Anna Botsford Comstock took a special interest in young Winifred, and Miss Bailor graduated in 1921, in a time when few women and virtually no black women had any higher education. She went down south to teach....she never taught again after she came back north in the 1920s. "Well, you had to go down south. You might have a degree, but there wasn't any colored teachers in schools here," she said. Wasn't that unfair? "Ohhhhh," she said. "That was the law. A colored teacher in a white school? No indeed.""