Brought up in the wilderness of New York state, Harding, as a lad of splendid physique, standing over 6 feet 3 inches, marched as a drummer with the militia to the St Lawrence in 1813. He became subsequently chairmaker, peddler, inn-keeper, and house-painter, painting signs in Pittsburg, Pa., and eventually going on the road, self-taught, as an itinerant portrait painter. From 1826-1830, he resided in Beacon Hill, Boston, Massachusetts, in what became known as the Chester Harding House, a National Historic Landmark which now houses the Boston Bar Association.
He made enough money to take him to the schools at the Philadelphia Academy of Design, and he soon became proficient enough to gain a competency, so that later he went to England and set up a studio in London. There he met with great success, painting royalty and the nobility, and, despite the lackings of an early education and social experience, he became a favourite in all circles. Returning to the United States, he settled in Boston and painted portraits of many of the prominent men and women of his time.