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Ashkelon (Hebrew אשקלון Aqəln; Arabic عسقلان Asqalān; traditional English Ascalon) was the oldest and largest seaport in ancient Canaan, one of the "five cities" of the Philistines, north of Gaza. The modern city of Ashqelon has been built near the ancient ruin, which remains unoccupied.

Archeological excavations began in 1985 led by Lawrence Stager of Harvard University are revealing the site with about 50 feet of accumulated rubble from successive Canaanite, Philistine, Phoenician, Hellenistic, Roman, Byzantine, Islamic, and Crusader occupation.

In the oldest layers are shaft graves of pre-Phoenician Canaanites. The city was originally built on a sandstone outcropping and has a good underground water supply. It was relatively large as an ancient city with as many as 15,000 people living inside walls a mile and a half long, 50 feet high and 150 feet thick. Ashkelon was a thriving Middle Bronze Age (2000-1550 BCE) already city of more than 150 acres, with commanding ramparts including the oldest arched city gate in the world, eight feet wide, and even as a ruin still standing two stories high. The thickness of the walls was so great that the mudbrick Bronze Age gate had a stone-lined tunnel-like barrel vault, coated with white plaster, to support the superstructure: it is the oldest such vault ever found.

The Bronze Age ramparts were so capacious that later Roman and Islamic fortifications, faced with stone, followed the same footprint, a vast semi-circle protecting Askalon on the landward side. On the sea it was defended by a high natural bluff.

Within the huge ramparts, in the ruins of a sanctuary, a votive silver calf was found in 1991. During the Canaanite period, a roadway more than 20 feet in width ascended the rampart from the harbor and entered a gate at the top. Nearby, in the ruins of a small ceramic tabernacle was found a finely cast bronze statuette of a bull calf, originally silvered, 4 inches long. Images of calves and bulls were associated with the worship of the Canaanite gods El and Baal (the "lord," whose name was translated into Hebrew as "Moloch"). Calf worship was execrated repeatedly by Old Testament prophets, a proscribed Canaanite religious practice that the Hebrews only too easily fell into. Besides the Golden Calf of Exodus, Hosea inveighs against kissing calf-images (Hosea 13:2).

The Philistines conquered Canaanite Ashkelon about 1150 BCE. Their earliest pottery is similar to pottery found at Mycenae in mainland Greece, adding weight to the hypothesis that the Mycenaeans and Philistines were among the "Sea Peoples" that upset cultures throughout the eastern Mediterranean at that time. Ashkelon became one of the five Philistine cities that were constantly warring with the Israelites and the kingdom of Judah. When this vast seaport, the last of the Philistine cities to hold out against Nebuchadnezzar finally fell in 604 BCE, burnt and destroyed and its people taken into exile, the Philistine era was over.

Ashkelon was soon rebuilt. It was an important Hellenistic seaport, the birthplace of Herod the Great who rebuilt and enrichedthe city and it continued to flourish in the Roman and Byzantine periods.

During the Crusades, Ashkelon (which was known to the Crusaders as Ascalon) was an important fortress. Although Fatimid forces were defeated at Ascalon by the Crusaders in 1099, the city itself was not taken. In 1150 it was fortified with fifty-three towers by its Egyptian Fatimid rulers, to defend it against marauding Crusaders, but to no avail, for it fell three years later, after a months-long siege, to Baldwin III of Jerusalem. It was then added to the County of Jaffa, one of the most important Crusader seigneuries. Saladin retrieved the strategic port for Islam after the Battle of Hittin, July 4, 1187, but with the Third Crusade a few years later, Saladin systematically demolished Ascalon lest it fall once more into the hands of the infidel. Indeed Richard the Lion-Hearted built a fort upon the ruins. Finally in 1270, the Mamluk sultan Baybars demolished Ascalon for the last time, filling in its harbor and leaving it desolate.

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