A slave holder who hired Douglass as a field hand when he was around seventeen years old. After living with Covey for a year, Douglass works for William Freeland and regards it as the best experience with an enslaver that he has ever had. There was a stark contrast between Freeland and Covey, and Douglass was never physically assaulted while living on Freeland’s farm. Freeland’s farm was about 3 miles from St. Michaels in Maryland.