In 1873, Hale began her formal art education and training in Boston with painter William Rimmer. Although the changing cultural and social landscape of Boston provided many new opportunities for women, female students were still segregated from their male counterparts. Therefore, Hale took private lessons from Rimmer, and his instruction focused primarily on drawing and the analysis of anatomy. A year later, Hale enrolled in William Morris Hunt's school for painting with approximately forty other women artists. With Hunt, artist Helen M. Knowlton acted as one of the school's main instructors. Hunt and Knowlton encouraged a new style and used unique teaching methods, such as interpretive sketching, which had an important artistic influence on Hale. Knowlton especially promoted a sense of community within the class of female artists, and the group of women relied upon each other, rather than their husbands or other men, for professional and personal support.