In 1804 James Brewster (born at Preston, Connecticut, 6 August 1788-died at New Haven, Connecticut, 22 November 1866, a seventh generation descendant of Elder William Brewster of the Mayflower colony) became an apprentice to carriage builder Colonel Charles Chapman when he was 16 years old. He considered pursuing a life in the military, achieving the rank of Lieutenant in the Northampton militia, but ultimately decided "coachmaker with a competency" sounded better than "General Brewster". James had $30 when he completed his apprenticeship, went to New York in 1809 but there were delays enroute.