Lillian Bailey was born in Columbus, Ohio on 17 January 1860 and was said to have demonstrated musical talent from an early age.
When she was 15, the family moved to Boston and she continued her studies under her uncle, Charles Hayden, a well-known vocal teacher and later she became a pupil of Madame Rudersdorf, with whom she studied two years.
[1] At sixteen, Bailey made her professional debut in Boston at one of B. J. Lang's concerts, meeting with great success.
After this she became a favorite singer in Boston, and her services were in constant demand during the concert season.
On April 30, 1879, she was among the performers in an orchestral concert in London, singing a solo number and a duet with George Henschel; he became her teacher, and married her on March 9, 1881.