The oldest remnants of human life in the Pelagonia valley date back to the Neolithic period, with the oldest representative of the Velushina-Porod culture dating back to the late Neolithic.
The numerous material discoveries from the archaeological sites (Velushina, Porodin, Beranci) show cultural layers of the Eneolithic, Bronze and Iron Age periods, while findings from the ancient city Heraclea Lyncestis (erected by Philip II in 349 BC), create a continuity of life to the Macedonian-Hellenistic and Roman periods.
After a millennium of existence, in the 6th century A.D. the life in the ancient Macedonian city of Heraclea ceased. It was the time of mass settlement of the Slavic tribes on the Macedonian territory.
In the immediate vicinity of Heraclea settled the Macedonian-Slavic tribe “Berziti”, or “Brsjacs”, who began to create a new Slavic settlement, which the foreigners variously called, such as: Butela, Butelion while the local Slavic population named it Bitolj (Битољ), which later was transformed into today’s modern name – Bitola.
During the reign of Tsar Samuil (Цар Самуил), his son Gavril Radomir and nephew Jovan Vladislav, there was a royal residence in Bitola. In a military campaign, the Byzantine emperor Basil II ordered that it would be set on fire, but the city was not taken.
Bitola, like other medieval towns, had its fortress to protect the population from military attacks. The fort was severely damaged. In 1015 the Emperor Gavril Radomir was assassinated by his cousin Emperor Jovan Vladislav, who was proclaimed emperor and in 1015/16 ordered the rebuilding of the city’s fortress.
On this occasion, a prominent marble slab with a Slavic text was placed at the entrance of the fortress, where the city with its Slavic name was mentioned for the first time. It says that he erected a town here called Obitel, which means a monastery or family of monks. This plaque was found in Solak – Singur Caus Mosque, and today is exibited in the Bitola Museum.
After the brief reign of Emperor Jovan Vladislav, Bitola and the whole empire fell under Byzantine rule. In 1019 Bitola is mentioned as the seat of a bishop who was under the church administration of the Ohrid bishopric mentioned in the work of Jovan Skilica “The Brief History” and the famous “Gramota” of Emperor Basil II, where Bitola is represented as an important Slavic city.
In the 12th century, William of Tyre (Latin: Willelmus Tyrensis) as part of the First Crusade, mentions Bitola as a large and beautiful city. In the middle of the 13th century, the Arab traveler Idrizi gives similar information in his work “Geography”, writing that Bitola is an important and beautiful city with a beautiful location.
Theophylact of Ohrid (Теофилакт Охридски) during the first half of the 14th century, described Bitola as a developed settlement with a feudal system, and developed trade with the cities Dubrovnik, Venice, Thessaloniki and Constantinople.
In the Middle Ages, Bitola also served as a Christian center for the Pelagonija region and beyond.
With the Turkish Ottoman invasion of the Balkan Peninsula, Bitola fell under Ottoman rule in 1382/3.
A 17th century Turkish chronicler noted in his work “Amazing Events”:
“… while the Prilep Fortress was conquered peacefully, the one in Bitola was conquered by force …“
During the conquest of the city of Bitola the Turks met with great resistance by the local population, but after several days the city was conquered by the army led by Timurtash Bey.
After the occupation of the city, the Bitola Fortress was destroyed to the ground. With a special decree from the Sultan Murat I the city was handed over to the management of Evronos Bey. In this period, Turkish documents mention Bitola under the names of Manastir (Monastery), Toli Manastir, Toli, Manastir and Monastir.
Due to its important geographical position, Bitola has become an important military-political and administrative-cultural center in this part of the Balkans.
In the period that followed the city was experiencing major ethnic changes, the Turkish population became the predominant population for which religious institutions were built – mosques, religious schools (medreses), bezistens, tekkes, inns, hammams, sarai (lavish houses). etc.