Wheelock was persuaded by Elizabeth Peabody to attend the Kindergarten Training School in Boston. She graduated in 1879, and became a kindergarten teacher in Chauncy Hall School, also in Boston.
In 1888, when Boston public schools added kindergartens, Wheelock began a one-year training program for teachers at Chauncy Hall. It began attracting students from other parts of the country, and, after expanding to two years, became an independent training school.
Later, the school added training for primary and nursery school teachers as well, and expanded the kindergarten course to three years in 1929.
Wheelock served on several crucial national committees that worked for recognition and standardization of kindergarten education and teacher training. She worked on kindergarten and education issues with settlement houses, the National Education Association, and the League of Nations.
She also translated Johanna Spyri stories and wrote a number of books on kindergarten education.
At her retirement in 1939, the Wheelock School was incorporated and became Wheelock College.