Her uncle was Charles Woodruff, a noted general in the United States Army.

[2] In 1925, she received an honorary master's degree in education at Middlebury College.

[3] Woodruff taught as a young woman, and was principal of Castleton Teachers' College from 1921 to 1940,[2][4] including during the 1924 fire that burned the school's main building.

[5] She was co-principal of the Green Mountain School for Girls,[1] and from 1937 to 1938 served as president of the National Education Association.

[16] Castleton University also presents a Caroline Woodruff Award as "the highest honor that a student leader can achieve".