As part of the rich Osogovo mining region, the Kratovo area is associated with the ancient names Kratiskara, Kratis, and Koriton, attested in later Byzantine sources. Even in antiquity, the surrounding hills were known for their gold, silver, lead, and copper deposits, exploited first by the Paeonians and later by the Romans, who left traces of mining activity throughout the wider region.
In the Middle Ages, Kratovo became a significant town in the Byzantine and later the Serbian Empire. Mining continued to be the main economic activity, and the town developed as a trading and craft center.
In the 16th and 17th centuries, Kratovo was one of the most important mining and minting centers in the European part of the Ottoman Empire — it even housed an imperial mint (darphane). Ottoman census registers (defters) from the 16th century document a dense settlement of several thousand inhabitants, a powerful artisans' bazaar, and a developed mining administration. During this period, most of the renowned towers and bridges that today symbolize the town were rebuilt and expanded.
Today Kratovo is a protected cultural heritage site and tourist destination. Hotel Kratis has been renovated, new restaurants have opened, and traditional houses are being adapted for tourist accommodation. The town is working on improving the river channels and sewage system to preserve its historical appearance.
Many researchers believe the towers were built during the Ottoman period, based on their architecture and decorative elements. They were constructed with mortar and semi-cut stone. Simiḱeva Tower at 21.95 meters is the tallest, while Saat Kula from ~1372 is the oldest preserved. Zlatkova Tower from ~1365, Krsteva Tower from 1371/72, Emin-begova Tower at 12 meters height, and Hadži-Kostova Tower conserved in 1957 — all tell stories of the rich past.
Once Kratovo had 17 bridges, and today 4 stone, 1 wooden, and 1 concrete bridge remain. The most famous is Radin Most from 1833, with a legend about a walled-in maiden named Rada. Grofčanski Bridge was built in the early 18th century, Čaršiski (Imperial) Bridge from 1804 was named after the sultan's visit, and Jokšinski Bridge from 1519 is among the oldest preserved.
Kratovo is one of the most important historical mining centers in the Balkans. From Roman times, and especially during the medieval and Ottoman periods, gold, silver, lead, and copper were mined and processed here. In the 16th–17th centuries the town also operated an Ottoman imperial mint (darphane), and contemporary defters record a population of several thousand — making Kratovo one of the most densely settled and prosperous market towns in the wider region of the Balkans of its time.