[Illustration of Penny Hill Doctor’s Office] Driving on Highway 33 near the Pitt/Edgecombe County line, a driver might see the remains of the small community known as Penny Hill. Once called “Winona” and later simply “Hill,” this community was the ancestral home of the Thigpen family. The doctors James Thigpen III and IV and James Thigpen V and VI all raised the families in Penny Hill. After this, the land and house changed hands to become the possessions of Dr. Phesanton S. Sugg and Dr. George C. Sugg. Their land totaled over 2,500 acres. These two gentlemen sold the land to Charles W. Smith who in time sold it back to a Thigpen. Captain James R. Thigpen bought the land and house from Mr. Smith in January 1873. In 1894, after finally reclaiming their ancestral home, the Thigpen’s lost their land and house again. Dr. James R. Thigpen was forced to sell it because of debts. The land thereafter was divided up, and this ended the Thigpen legacy in Penny Hill.