Hale's earliest training was under his sister Ellen Day Hale at the Museum of Fine Arts, Boston, then at the Ecole des Beaux-Arts and Academy Julian in Paris, as well as with the artists William M. Chase, J. A. Weir, and Kenyon Cox.
Hale would go on to teach at the School of the Museum of Fine Arts, Boston for 30 years. He also spent time writing art criticism.
He died in 1931.