Heraclea Lyncestis in the context of "Ancient Greek architecture"

Under the reign of Philip II (359–336 BC), the ancient kingdom of Macedonia, initially at the periphery of classical Greek affairs, came to dominate Ancient Greece in the span of less than 25 years, largely thanks to the character and policies of its king. In addition to utilising effective diplomacy and marriage alliances to achieve his political aims, Philip II was responsible for reforming the ancient Macedonian army into an effective fighting force. The Macedonian phalanx became the hallmark of the Macedonian army during his reign and the subsequent Hellenistic period. His army and engineers also made extensive use of siege engines. Chief among Philip's Thracian enemies was the ruler Kersebleptes, who may have coordinated a temporary alliance with Athens. In a series of campaigns stretching from 356 to 340 BC, Philip II managed to ultimately subjugate Kersebleptes as a tributary vassal, conquering much of Thrace in the process. Philip II also fought against the Illyrian king Bardylis, who threatened Macedonia proper, and against Grabos II and Pleuratus in Illyria (centred in modern-day Albania). In his newly conquered territories, he founded new cities such as Philippi, Philippopolis (modern Plovdiv, Bulgaria), Herakleia Sintike (Pirin Macedonia, Bulgaria), and Herakleia Lynkestis (modern Bitola, North Macedonia).

Philip II eventually campaigned against the city-state of Athens and her allies in the Aegean region, as well as Thebes after the decline of its hegemony in mainland Greece. In the defence of the Amphictyonic League of Delphi and in conjunction with the Thessalian League, Macedonia became a key player in the Third Sacred War (356–346 BC), defeating the Phocians, commanded by Onomarchus, at the Battle of Crocus Field in 352 BC. While poised to launch a direct assault on Athens in 346 BC, the Macedonian king was met with an Athenian embassy that arranged the Peace of Philocrates. As a result, Macedonia and Athens became allies, yet Athens was forced to relinquish its claims to the city of Amphipolis (in modern-day Central Macedonia).

Bitola (/ˈbiːtoʊlə, -tələ/; Macedonian: Битола [ˈbitɔɫa] ) is a city in the southwestern part of North Macedonia. It is located in the southern part of the Pelagonia valley, surrounded by the Baba, Nidže, and Kajmakčalan mountain ranges, 14 kilometres (9 miles) north of the Medžitlija-Níki border crossing with Greece. The city stands at an important junction connecting the south of the Adriatic Sea region with the Aegean Sea and Central Europe, and it is an administrative, cultural, industrial, commercial, and educational centre. It has been known since the Ottoman period as the "City of Consuls", since many European countries had consulates in Bitola.

Bitola, known during the Ottoman Empire as Manastır or Monastir, is one of the oldest cities in North Macedonia. It was founded as Heraclea Lyncestis in the middle of the 4th century BC by Philip II of Macedon. The city was the last capital of the First Bulgarian Empire (1015–1018) and the last capital of Ottoman Rumelia, from 1836 to 1867. According to the 2002 census, Bitola is the third largest city in the country, after the capital Skopje and Kumanovo. Bitola is also the seat of the Bitola Municipality.