Born in Cincinnati, Charles Allan Winter enrolled in the Cincinnati Art Academy at a young age. He was awarded a Foreign scholarship from the school in 1894 to study at the Académie Julian in Paris under William-Adolphe Bouguereau and Gabriel Ferrier, as well as a scholarship to study in Rome. Returning to this country, he taught portraiture at the St. Louis School of Fine Art from 1898 to 1901. It was there that he met his future wife Alice Beach who was also an artist.

In 1901, the Winters settled in New York where he worked as a portrait painter and as a magazine illustrator including with "The Masses." During this time, like many painters, Winter began experimenting with various color theories and technical approaches to painting using geometric principals to strengthen his compositions. It was around 1910 that the Winters made their first summer visit to Gloucester and Cape Ann. Enamored with the area, they convinced John Sloan and his wife Dolly who they had befriended in New York to also visit. In 1922, the Winters had a house and studio built on Mount Pleasant Avenue in East Gloucester; they made this their year-round home in 1931.

Charles Allan Winter was employed during the 1930s as a mural painter under the auspices of the Works Progress Administration. Examples of his murals are preserved within Gloucester’s City Hall.