As well as the main cities in the area - Pesaro, Fano, Urbino and Senigallia – other smaller towns also have Roman origins, such as Fossombrone, Cagli, Urbania, Macerata Feltria and Pennabilli. During the Middle Ages and the Renaissance, these towns took on their current form which can be admired in the historic centres with their beautifully preserved churches, palaces, towers and fortifications.
New settlements sprang up during the medieval period, mainly built to ensure control of the region. The traces or structures of the castles and walled towns can still be seen despite subsequent transformations in later periods. Some of them, which were strategically important, have imposing walls and stronghold, such as Gradara. The castle and walled town of Gradara dominate the hills of the inland area extending to the nature reserve of San Bartolo, while other fortified settlements consist of a group of houses surrounded by defensive walls, protecting the local population who lived in the fertile surrounding countryside.
During the Renaissance, many towns and settlements were enlarged and embellished and the medieval buildings were refined with arches and columns. Further transformations and extensions took place over the following centuries without radically altering the original layout. After the Second World War, regulations were introduced to protect the historic centres of small towns and villages which have been well-preserved and carefully restored.