He was the first painter to spend any significant amount of time in Connecticut, and was active in Portsmouth, New Hampshire as well.
[2] He began his career as a musician, serving as organist at Boston's Christ Church from 1750 to 1753, before he decided to become a painter.
He then moved to Connecticut, remaining in the colony for at least three years; during his sojourn there he worked in New London, New Haven, and the area around Hartford.
[1] He was the first painter to work there – residents previously having to travel to Boston, Newport, or New York City to be painted – and may have been lured there by his sister, Susan Hobby, who lived in Middletown.
[1] He was generally comfortable working in a three-quarter length format; his greatest difficulty lay in attaching the sitter's head to the body.