Ashkelon, one of the five major Philistine cities, is frequently mentioned in the Old Testament. Located on the Mediterranean coast, it was a significant center of trade and military power. The city is first mentioned in the context of the Philistine pentapolis, which included Gaza, Ekron, Ashdod, and Gath (Joshua 13:3). Ashkelon was known for its idolatry and opposition to Israel. In Judges 14:19, Samson famously struck down thirty men in Ashkelon to settle a wager. The prophets often pronounced judgment against Ashkelon for its wickedness and enmity towards Israel. Zephaniah 2:4-5 declares, "For Gaza will be abandoned, and Ashkelon will lie in ruins. At midday Ashdod will be emptied, and Ekron uprooted." The city was eventually conquered by the Babylonians and later by the Greeks and Romans.

Gaza

Gaza, another principal city of the Philistines, is located in the southwestern part of modern-day Israel near the Mediterranean Sea. It is one of the oldest cities in the world, with a history of conflict and conquest. In the Bible, Gaza is often associated with the Philistines' oppression of Israel. Samson's exploits in Gaza are well-known; he carried away the city gates (Judges 16:1-3) and later met his demise there after being captured and blinded by the Philistines (Judges 16:21-30). The prophets also foretold the destruction of Gaza. Amos 1:6-7 states, "For three transgressions of Gaza, even four, I will not revoke My judgment, because they exiled a whole community, handing them over to Edom. So I will send fire upon the walls of Gaza, to consume its citadels." Despite its turbulent history, Gaza remained a significant city through various empires.

Ekron

Ekron was one of the five cities of the Philistine confederation, located inland from the Mediterranean coast. It is mentioned in the context of the Philistine territory in Joshua 13:3. Ekron is perhaps best known for its association with the Ark of the Covenant. After capturing the Ark, the Philistines brought it to Ekron, but it brought calamity upon the city, leading the Ekronites to send it back to Israel (1 Samuel 5:10-12). The city was also a center of idolatry, as seen in 2 Kings 1:2-3, where King Ahaziah of Israel sent messengers to inquire of Baal-Zebub, the god of Ekron. The prophet Zephaniah prophesied against Ekron, saying it would be uprooted (Zephaniah 2:4). Like the other Philistine cities, Ekron faced destruction and conquest by successive empires.

Ashdod

Ashdod, another key city of the Philistine pentapolis, was located on the Mediterranean coast. It was a major port and a center of commerce and military strength. Ashdod is mentioned in the context of the Philistine territory in Joshua 13:3. The city is notable for its temple of Dagon, where the Philistines placed the captured Ark of the Covenant, leading to the idol Dagon falling before the Ark (1 Samuel 5:1-5). The prophets frequently pronounced judgment against Ashdod for its idolatry and opposition to Israel. In Isaiah 20:1, the Assyrian king Sargon captured Ashdod, fulfilling prophetic warnings. Zechariah 9:6-7 also foretells the downfall of Ashdod, saying, "A mixed race will occupy Ashdod, and I will cut off the pride of the Philistines." Despite its eventual decline, Ashdod remained an important city through various historical periods.