We can help you with your concerns. Pittsboro Pittsboro is located in south of Chapel Hill and is called a "Circle City". The reason Pittsboro is called a "Circle City" is because the roundabout surrounds the Chatham Historical Museum in the center of Pittsboro. Known for its historic downtown, picturesque landscape, and vibrant community, Pittsboro blends rural beauty with cultural attractions. Pittsboro is characterized by the following features. History and Culture Downtown: The town's historic downtown features quaint stores, local restaurants, art galleries, and historic buildings. It is also a center for community events, farmers markets, and festivals. Chatham County ...