A graduate of Oberlin College, Fairbank had assisted more than 43 slaves across the Ohio River by the time he was 28 years old. He and Delia Webster assisted the Lewis Hayden family to freedom before being caught on their return trip from Maysville to Lexington, Kentucky. Fairbank served four years in the Kentucky state penitentiary before he was pardoned. As soon as he was released, he continued his Underground Railroad activities until he was arrested for assisting a fugitive woman from Louisville for which he was convicted and served 13 years. During those years in prison he worked in the hemp factory and received numerous beatings.