The ancient city of Megiddo was an strategic fortress and town located in the most important ancient roads exchanges, the Via Maris was connected right here to the ancient roman road from Caesarea Maritime and the region of Syria, Babylon and Assira.
The book of Revelations describe the final battle between the force of evil and force of God in this incredible and strategical region in the Holy Land.
The future mourning of Israel over her Messiah is likened, in the second place (cf. v. 10), to the weeping on the day when godly King Josiah, the last hope of the fading Judean nation, was slain by Pharaoh Neco II, at Hadad Rimmon, traditionally identified as a village near Jezreel, in the plain of Megiddo (cf. 2 Chron. 35:20-27). Thus the greatness of the mourning at this final outpouring of the Holy Spirit can be compared only to the weeping of a most extreme individual (Zech. 12:10) and to corporate (v. 11) catastrophes of the nation.
F. Duane Lindsey, Zechariah (The Bible Knowledge Commentary; ed. John F. Walvoord and Roy B. Zuck; Wheaton: Victor Books, 1985), 1:1567.
Megiddo: place of troops, originally one of the royal cities of the Canaanites (Josh. 12:21), belonged to the tribe of Manasseh (Judg. 1:27), but does not seem to have been fully occupied by the Israelites till the time of Solomon (1 Kings 4:12; 9:15).
The valley or plain of Megiddo was part of the plain of Esdraelon, the great battle-field of Palestine. It was here Barak gained a notable victory over Jabin, the king of Hazor, whose general, Sisera, led on the hostile army. Barak rallied the warriors of the northern tribes, and under the encouragement of Deborah (q.v.), the prophetess, attacked the Canaanites in the great plain. The army of Sisera was thrown into complete confusion, and was engulfed in the waters of the Kishon, which had risen and overflowed its banks (Judg. 4:5).
Many years after this (B.C. 610), Pharaohnecho II., on his march against the king of Assyria, passed through the plains of Philistia and Sharon; and King Josiah, attempting to bar his progress in the plain of Megiddo, was defeated by the Egyptians. He was wounded in battle, and died as they bore him away in his chariot towards Jerusalem (2 Kings 23:29; 2 Chr. 35:22-24), and all Israel mourned for him. So general and bitter was this mourning that it became a proverb, to which Zechariah (Zech. 12:11, 12) alludes. Megiddo has been identified with the modern el-Lejjun, at the head of the Kishon, under the north-eastern brow of Carmel, on the south-western edge of the plain of Esdraelon, and 9 miles west of Jezreel. Others identify it with Mujedd’a, 4 miles south-west of Bethshean, but the question of its site is still undetermined.
“MEGIDDO,” Easton’s Bible Dictionary, n.p.
The Armageddon appear only in Rev. 16:16 (R.V., “Har-Magedon”), as symbolically designating the place where the “battle of that great day of God Almighty” (ver. 14) shall be fought. The word properly means the “mount of Megiddo.” It is the scene of the final conflict between Christ and Antichrist. The idea of such a scene was suggested by the Old Testament great battle-field, the plain of Esdraelon (q.v.).
“ARMAGEDDON,” Easton’s Bible Dictionary, n.p.
The Battle of Armageddon
“And the sixth angel poured out his vial upon the great river Euphrates; and the water thereof was dried up, that the way of the kings of the east might be prepared. And I saw three unclean spirits like frogs come out of the mouth of the dragon, and out of the mouth of the beast, and out of the mouth of the false prophet. For they are the spirits of devils, working miracles, which go forth unto the kings of the earth and of the whole world, to gather them to the battle of that great day of God Almighty. Behold, I come as a thief. Blessed is he that watcheth, and keepeth his garments, lest he walk naked, and they see his shame. And he gathered them together into a place called in the Hebrew tongue Armageddon.”
Revelation 16:12–16 KJV
This battle is to take place “after a long time” and “in the...last days”—both consistent references to the end-time (cp. Jr 4:6,13,24–26; 5:15; 6:1,22; 10:22; 23:20; Dn 8:26; 10:14). The confederacy will come into the land “that has been restored from war and regathered from many peoples,” a reference to regathered Israel. Gog will devise an evil plan against Israel. According to Rv 20:1–10, this battle may be in two parts: one at the end of history (Rv 19:17–21) and one after a thousand years of peace (Rv 20:1–3). Gog and Magog, along with Satan, will be fully and finally defeated (Rv 20:7–10). Ezekiel’s battle may be the first battle, or the second, or both. Gog will loot and plunder those who dwell in “open villages” at “the center” (Hb tabor), possibly the region around Mount Tabor just north of the Valley of Jezreel, site of the battle of Armageddon (Rv 16:16). Motivated by vengeance and greed, Gog will attempt the annihilation of Israel (v. 16).
Ted Cabal, ed., The Apologetics Study Bible (Accordance electronic ed. Nashville: Holman Bible Publishers, 2007), n.p.