Due to the limited documentation available, it is difficult to accurately trace the history of Isola Dovarese. However, these documents suggest an undisciplined population that was uncooperative with the authorities. This necessitated the construction of prisons in the inner courtyard of the Town Hall.
It is likely that the prisons in Isola Dovarese were built in conjunction with the square and other associated structures. These prisons were also used to detain brigands who often passed through the village from the river trade piers. Because of the limited size of Isola Dovarese and its susceptibility to flooding, the inhabitants tended to focus their efforts on trade and crafts rather than agriculture.
The river landing at Isola Dovarese was of great importance for trade in the region because of the difficulty of navigating upstream. The small merchant boats that docked at Cavallatico carried items such as seeds, but were also used to transport criminals, who were often taken into custody by customs officers. Evidence of this can be seen in the carvings on the plaster of low keel boats used for river navigation.