Masefield was born in Ledbury, a rural area in England to George Masefield, a solicitor and Caroline. His mother died giving birth to his sister when Masefield was only 6 and he went to live with his aunt. His father died soon after. After an unhappy education at the Kings School in Warwick (now known as Warwick School), where he was a boarder between 1888 and 1891, he left to board the HMS Conway, both to train for a life at sea, and to break his addiction to reading, of which his Aunt thought little. He spent several years aboard this ship and found that he could spend much of his time reading and writing. It was aboard the Conway that Masefield’s love for story-telling grew.

In 1894, Masefield boarded the Gilcruix, destined for Chile. He recorded his experiences while sailing through the extreme weather. Upon reaching Chile, Masefield suffered from sunstroke and was hospitalized. He eventually returned home to England as a passenger aboard a steam ship.

In 1895, Masefield returned to sea on a windjammer destined for New York City. However, the urge to become a writer and the hopelessness of life as a sailor overtook him, and in New York, he deserted ship. He lived as a vagrant for several months, before returning to New York City, where he was able to find work as an assistant to a bar keeper.

For the next two years, Masefield was employed in a carpet factory, where long hours were expected and conditions were far from ideal. He purchased up to 20 books a week, and devoured both modern and classical literature. His interests at this time were diverse and his reading included works by Trilby, Dumas, Thomas Browne, Hazlitt, Dickens, Kipling, and R. L. Stevenson. Chaucer also became very important to him during this time, as well as poetry by Keats and Shelley.

When Masefield was 23, he met his future wife, Constance Crommelin, who was 35. Educated in classics and English Literature, and a mathematics teacher, Constance was a perfect