Stephen Reynolds was born to Enos and Sarah Reynolds on November 17, 1782 in Andover, Massachusetts. In 1810 he sailed as a seaman on the brig New Hazard on a trading expedition to the Pacific Northwest, Hawaii and Canton, China. Although he was not the official log keeper for this voyage, his journal is the only remaining record and was published in 1938. In 1817, he sailed on the ship Ida, to the Northwest Coast. He was also a log keeper for a voyage from New York to Canton on the ship Adonis in 1821. In 1823 he moved to Honolulu and served as a clerk for merchant William French. He went into business for himself in 1829 as a trader of at first sandalwood and then general merchandise.

Reynolds had a domestic partnership with Winshipa Harbottle (died 1829), which produced two children: William Pitt (1827-1888) and Maria Harriet (1828-1828). He then married Susan Kukunaneki Jackson (died 1881), a daughter of the missionary Edward Jackson, in August of 1829. This union produced five children: Matilda Euela (1830-1916); Evaline (1831-1856); John Rice (1833-1855); Harriette (1835-1890); and Edward Jackson (1838-1868). All of his children were sent to Reynold's sisters in Boxford, Massachusetts for education at about the time they reached 3 years old.

Throughout the journal, Reynolds wrote about symptoms of illness. After a period of attempted respite in California he returned to Honolulu where he was found to be unable to manage his affairs by a jury of peers. His sister Rebecca traveled to Honolulu to retrieve him in 1856 and he died in Boxford, on July 17, 1857.

For a more robust biography, please refer to the biography on page ix in King's Journal of Stephen Reynolds.