Lilian Westcott Hale was born in Hartford. She first studied painting in private lessons and at the Hartford Art School; and, when she was in her teens, she spent a summer at William Merritt Chase's art school at Shinnecock on Long Island. At 18 she began five years of study at the Museum of Fine Arts School in Boston. Within a few years she was participating in important exhibitions, and had her first solo show at a Boston gallery in 1908. She also showed in New York galleries and in many other exhibitions. Although Hale produced many landscapes, she was known primarily as a portraitist, and continued to execute portraits until late in her life.