Adullam
At one time Adullam was a Canaanite royal city. It is also the location where King David hid in a cave from King Saul (1Samuel 22:1, 2Samuel 23:13).
Ai
Ai was the second city taken by ancient Israel after they entered the Promised Land (Joshua 7:3 - 5, 8:1, 9:3, etc.).
Beersheba
Beersheba is the name Abraham gave the location where he dug a well and made a covenant with Abimelech (Genesis 21:31 - 32). It is also the location where Hagar and her son journeyed to after being cast out of Abraham's household (Genesis 21:14). In the Old Testament, it is frequently referenced as the most southern city of ancient Israel (Judges 20:1, 1Samuel 3:20, 2Samuel 24:2, etc.).
Beth Horon (Bethhoron in King James Bible)
The location where God miraculously had the sun and moon stand still, for several hours, in order to allow Joshua more time to fight the Amorites (Joshua 10).
Bethel
Jacob (Israel) renamed Luz to Bethel ("the house of God") after he saw a miraculous vision of a ladder going up to heaven (Genesis 28:11 - 19, 31:13). It was also one of the Old Testament cities the prophet Samuel visited each year in his capacity as Israel's Judge (1Samuel 7:15 - 16). In a foolish attempt to retain his power, King Jeroboam of Israel set up a pagan idol in the city to keep people from going to Jerusalem to worship God (1Kings 12:27 - 29).
Bethlehem
Bethlehem is the ancestral home of Ruth and King David. It is also the location where Jesus Christ was born in 5 B.C. (Ruth 1:1, Matthew 2:1).
Brook Cherith
The brook Cherith is the place where ravens miraculously fed Elijah during a drought (1Kings 17:3, 5).
Dothan
Dothan is where Joseph, one of the children of Jacob (Israel), is sold into slavery by his brothers (Genesis 37:17).
Egypt
Jacob and his entire family move from Canaan to Egypt in order to escape a great famine in the land. They are taken care of by Joseph, one of Jacob's sons, who has been promoted by Pharaoh to be a ruler over the people (see Genesis 39 - 41).
Gaza
Gaza is the location where Samson, in the last use of his miraculous strength, sacrifices his life to destroy the Philistines' pagan temple to Dagon and the 3,000+ people within it (Judges 16:21 - 30).
Haran
Haran was one of Abram's (Abraham's) brothers. After his death in Ur, his father Terah takes his family (Abram, Sarai, Lot, etc.) to the land of Canaan where they name a city after him (Genesis 11:26 - 32). Haran is also the place where Jacob works for Laban in order to marry his daughters (Genesis 27:43, 28:7, 31:17 - 21).
Jericho
Jericho is the first city attacked, in the Promised Land, by Joshua and the children of Israel. God miraculously causes the walls of the city to come down after the people walk around them for six days as trumpets are being blown (Joshua 6).
Jerusalem
Jerusalem (formerly Jebus) is the place where Melchizedek blesses Abraham and where Abraham offers his only son Isaac as a sacrifice to God. The city, in the time of David, is conquered and made the capital of ancient Israel (1Chronicles 11:5).
Mount Carmel
Carmel is the place where Elijah the prophet has a confrontation with the prophets of Baal and is victorious (1Kings 18:20 - 42).
Mount Gilboa
It is on Mount Gilboa that King Saul and his son Jonathan are killed in battle (1Samuel 31:11, 2Samuel 1:6).
Mount Nebo
Moses, after wandering the wilderness forty years with the children of Israel, dies on Nebo after God allows him to see the Promised Land (Deuteronomy 32:49 - 50, 34:1).
Mount Tabor
Tabor is the place where Judges Deborah and Barak defeat the army of Sisera (Judges 4:14).
Peniel
Peniel is the location where Jacob wrestled an "angel" who was actually a pre-incarnate manifestation of Jesus Christ (Genesis 32).
Philistines
The Philistines were the fiercest, longest and greatest enemies of ancient Israel. Goliath the giant, whom a young King David defeated, was a Philistine.
Shechem
Shechem was one of Israel's six cities of refuge designated by God (Joshua 20:7).
Shunem
Shunem is the place where Elisha the prophet raised from the dead the son of a Shunammite woman (2Kings 4).
Sodom
Sodom, and its Old Testament sister city Gomorrah, experience God’s wrath for their many sins by being destroyed (Genesis 19).