Painter and printmaker William Sherwood was born on February 13, 1875, in Baltimore, Maryland. His grandfather, William Spencer Sherwood, owned and operated the first color printing business in Baltimore, which served much of Maryland and other Southern states for several decades. Sherwood first studied at St. John's College, Annapolis, from 1889 - 1893, leaving early to study under Howard Pyle in Delaware. He would later study at the Antwerp Royal Academy of Fine Arts, Belgium, as well.

In 1900 Sherwood's drawings published for the first time in the novel The Song of a Vagabond Huntsman by Irish novelist Charles Lever. This led to critical praise and further commissions, and in 1904, after marrying Mabel Houlkes-Jones, he worked as a figure painter in New Jersey and Manhattan. In 1910 the Sherwoods relocated to Belgium, living in Antwerp and spending summers in Bruges. Sherwood had his first solo exhibition in Brussels in 1913.

During World War I the city of Antwerp received heavy bombing during the seige by German, British, and French armies in 1914. Sherwood refused to flee and leave his work,and thus took shelter with his wife and neighbors in their cellar. After nearly two weeks, he obtained special permission from German forces to leave the city, and they managed to save his paintings, taking them via horse and cart across the border. They returned to the U.S., settling temporarily in New York until it was safe to return to Belgium. In the meantime he continued to paint, print, and exhibit, with some of his works proving to be the last visual accounts of French and Flemish towns that no longer stood, due to bombing during the war. By the time he returned to Europe in the 1920s he had established a reputation as a sought-after American artist who painted in the Flemish style.

A retrospective of Sherwood's work was held in Antwerp in 1931, and in recognition of his work he was given the title of Chevalier de l'Ordre de la Couronne by King Albert of Belgium. He identified as a Belgian and lived with his wife in quiet solitude for much of his career, and rarely made efforts to show in country of his birth outside of membership exhibitions with the Chicago Society of Etchers and the Printmakers of California. However, in 1934 the Baltimore Museum of Art held an exhibition of his work to much acclaim. He continued to work until his death in Bruges, Belgium, in 1951.

Sherwood's work is held in the collections of the Belgian government, the Musee Plantin Moretus Antwerp, the Library of Congress, the Cleveland and Detroit Public Libraries, the Worcester Free Library, and the Chicago Institute of Art, among others.