Howland was born on May 28, 1941, in Boston. At the age of 16, she left home and followed a dancer friend to New York City. After a time of struggling, Howland made her Broadway debut in 1959 as Lady Beth in the Carol Burnett musical Once Upon a Mattress, which transferred from off-Broadway. She went on to have roles in the musicals Bye Bye Birdie, High Spirits, Drat! The Cat! and Darling of the Day.