Ancient and early Byzantine periods
The area of the town is located in ancient Lynkestis, a region of Upper Macedonia, which was ruled by semi-independent chieftains till the later Argead rulers of Macedon. The tribes of Lynkestis were known as Lynkestai. They were a Greek tribe and belonged to the Molossian group of the Epirotes.There are important metal artifacts from the ancient period at the necropolis of Crkvishte near the village of Beranci. Heraclea Lyncestis was an important settlement from the Hellenistic period till the early Middle Ages. It was founded by Philip II of Macedon by the middle of the 4th century BC, and named after the Greek demigod Heracles, whom Philip considered his ancestor. With its strategic location, it became a prosperous city. The Romans conquered this part of Macedon in 148 BC and destroyed the political power of the city. However, its prosperity continued mainly due to the Roman Via Egnatia road which passed near the city. Several monuments from the Roman times remain in Heraclea, including a portico, thermae (baths), an amphitheater and a number of basilicas. The theatre was once capable of housing an audience of around 3,000 people.In the early Byzantine period (4th to 6th centuries AD) Heraclea was an important episcopal centre. Some of its bishops were mentioned in the acts of the Church Councils, including Bishop Evagrius of Heraclea in the Acts of the Sardica Council of 343 AD. A small and a great (Large) basilica, the bishop's residence, and a funeral basilica near the necropolis are some of the remains of this period. Three naves in the Great Basilica are covered with mosaics of very rich floral and figurative iconography; these well preserved mosaics are often regarded as fine examples of the early Christian art period. During the 4th and 6th centuries, the names of other bishops from Heraclea were recorded. The city was sacked by Ostrogothic forces, commanded by Theodoric the Great in 472 and, despite a large gift to him from the city's bishop, it was sacked again in 479. It was restored in the late 5th and early 6th centuries. In the late 6th century the city suffered successive attacks by Slavic tribes and was gradually abandoned.
Middle Ages
In the 6th and 7th centuries, the region around Bitola experienced a demographic shift as more and more Slavic tribes settled in the area. In place of the deserted theater, several houses were built during that time. The Slavs also built a fortress around their settlement. Bitola became a part of the First Bulgarian Empire from late 8th to early 11th centuries. The spread of Christianity was assisted by St. Clement of Ohrid and Naum of Preslav in the 9th and early 10th centuries. Many monasteries and churches were built in the city.In the 10th century, Bitola was under the rule of tsar Samuil. He built a castle in the town, later used by his successor Gavril Radomir of Bulgaria. The town is mentioned in several medieval sources. John Skylitzes's 11th century chronicle mentions that Emperor Basil II burned Gavril's castles in Bitola, when passing through and ravaging Pelagonia. The second chrysobull (1019) of Basil II mentioned that the Bishop of Bitola depended on the Archbishopric of Ohrid. During the reign of Samuil, the city was an important centre in the Bulgarian state and the seat of the Bitola Bishopric. In many medieval sources, especially Western, the name Pelagonia was synonymous with the Bitola Bishopric, and in some of them Bitola was known under the name of Heraclea due to the church tradition that turned the Heraclea Bishopric into the Pelagonian Metropolitan's Diocese. In 1015, tsar Gavril Radomir was killed by his cousin Ivan Vladislav, who declared himself tsar and rebuilt the city fortress. To celebrate the occasion, a stone inscription written in the Cyrillic alphabet was set in the fortress; in it the Slavic name of the city is mentioned: Bitol. As a military, political and cultural center, Bitola played a very important role in the life of the medieval society in the region, prior to the Ottoman conquest in the mid-14th century.On the eve of the Ottoman conquest, Bitola (Monastir in Ottoman Turkish) experienced great growth with its well-established trading links all over the Balkan Peninsula, especially with big economic centers like Constantinople, Thessalonica, Ragusa and Tarnovo. Caravans of various goods moved to and from Bitola.
Ottoman rule
For several centuries, Turks were a majority in this city, while the villages were populated mostly with Slavs. Evliya Çelebi says in his Book of Travels that the city had 70 mosques, several coffee-tea rooms, a bazaar (market) with iron gates and 900 shops. Manastır became a sanjak centre in the Rumelia Eyalet (Ottoman province).
Traditionally a strong trading center, Bitola is also known as "the city of the consuls". At one time (1878-1913) during the Ottoman rule, Bitola had consulates from twelve countries.During the same period, there were a number of prestigious schools in the city, including a military academy that, among others, was attended by the famous Turkish reformer Kemal Atatürk. Bitola was also the headquarters of many cultural organizations that were established at that time. In 1894, Manastır was connected with Thesaloniki by train. The first motion picture made in the Balkans was recorded by the Aromanian Manakis brothers in Manastır in 1903. In their honour, the annual Manaki Brothers International Film Camera Festival is held in modern Bitola.
Bitola during the Ilinden rebellion & the world wars
The Bitola region was a stronghold of the Ilinden Uprising. After the Balkan wars (1912-1913) and the division of the Ottoman province of Macedonia, Bitola got into the borders of Serbia, and during the First World War, it was almost burned down, since it was near the Macedonian Front (1916-1918). 25,000 inhabitants of Bitola have died and left.During the Second World War, the Germans and later Bulgarians took control of Bitola. On November 4th 1944, the 7th Macedonian Liberation Brigade entered Bitola victoriously.