The region around Montana became part of the Roman province of Upper Moesia in 29 BC. Around 160, the military camp that was most likely founded on the remains of an older Thracian settlement, acquired city rights under the name of Municipio Montanensium. The city developed and urbanized after a Roman model and became the second most important settlement in the province after Raciaria (modern-day Archar). A fortress was built on top of the hill over Montana, as well as public and residential buildings, temples, baths and theatres. Montana became a typical imperial settlement, where the local romanized population coexisted along Italic and Anatolian settlers. The base of the town’s economy were the big landowners of Italic origin and their villas and mansions, where the locals served to obtain agricultural production and gold from Ogosta’s river valley. A stratum of Greek settlers, who engaged in craftsmanship and money-landing existed in the town during the period. The patrons of Montana in the spirit of Hellenism were Diana and Apollo.

Middle Ages
Between 440 and 490, the northwest of modern Bulgaria was devastated by the raids of the Huns under Attila and the Goths. Slavs and Avars delivered the final strike on the Greco-Roman culture in the region, and the Slavs that settled in the area called the town Kutlovitsa. During the time of the First and Second Bulgarian Empires, the settlement recovered and became the centre of an eparchy.

Ottoman Rule
After Kutlovitsa was seized by the Ottomans, the settlement was destroyed and became deserted. Between 1450 and 1688, the town was resettled by Turks because of its strategic location, and went through another period of blossoming as a typically Oriental town. One mosques, fountains, and other new buildings were erected. The Turks’ suppression of the 1688 Chiprovtsi Uprising solidified the position of Kutlovitsa as a Turkish ethnic area in the 18th and 19th centuries]].There was also a Roman Bath left over the Middle Ages

Modern History
After the Liberation began a massive wave of migration towards Kutlovitsa and a period of economic blossom. An electric station, a train station, a post office and a hospital were built, a fair and a community centre emerged.

Names
Kutlovitsa was renamed to Ferdinand in 1890, receiving the benevolence of Bulgarian Knyaz Ferdinand and a city status. In 1945, communist authorities changed the town’s name to Hristo Mihaylov after red party activist Hristo Popmihaylov that died in 1944, who was born there. A year later the name was changed to Mihaylovgrad. In 1993, after a presidential decree, the town received the name Montana, inspired by its antic name.