Ernest Longfellow was born in Cambridge, Massachusetts, raised at Craigie House and educated at Harvard College. He was the second of six children. His professional life was spent in Boston with frequent visits to Europe.
He exhibited at the National Academy of Design in 1871 and 1875; the Williams and Everett Gallery in Boston in 1875; the 1876 World’s fair in Philadelphia; and Boston’s Museum of Fine Art and the St. Botolph Club in 1880. He belonged to the Boston Art Club and moved to New York around the turn of the century.
He died in November 1921 at the Hotel Touraine in Boston and his funeral service was held at Craigie House. Longfellow bequeathed some 55 paintings from his collection to the Museum of Fine Art, Boston, including works by Jacopo Bassano, John Constable, Thomas Couture, Luca Giordano and others.