Overview:
The entry into the Promised Land marks a pivotal moment in the history of Israel, fulfilling God's covenant promise to Abraham, Isaac, and Jacob. This event is primarily chronicled in the Book of Joshua, where the Israelites, under Joshua's leadership, cross the Jordan River and begin to take possession of Canaan, the land promised to their forefathers.

Biblical Context:
The journey to the Promised Land begins with God's promise to Abraham in Genesis 12:7: "The LORD appeared to Abram and said, 'To your offspring I will give this land.'" This promise is reiterated to Isaac and Jacob, establishing a divine covenant that the descendants of Abraham would inherit the land of Canaan.

After centuries of slavery in Egypt, the Israelites are delivered by God through Moses, as recounted in the Book of Exodus. Despite their liberation, the Israelites wander in the wilderness for 40 years due to their disobedience and lack of faith, as described in Numbers 14:33-34.

Crossing the Jordan:
The actual entry into the Promised Land occurs in the Book of Joshua. Joshua 3:14-17 describes the miraculous crossing of the Jordan River: "So when the people broke camp to cross the Jordan, the priests carried the ark of the covenant ahead of them. Now the Jordan overflows its banks throughout the harvest season. But as soon as the priests carrying the ark reached the Jordan and their feet touched the water’s edge, the water flowing downstream stood still, rising up in a mass that extended as far as Adam, a city near Zarethan. The water flowing downstream into the Sea of the Arabah (the Salt Sea) was completely cut off, and the people crossed over opposite Jericho."

Conquest and Settlement:
Following the crossing, the Israelites begin the conquest of Canaan, starting with the famous Battle of Jericho, where the walls of the city fall after the Israelites march around them for seven days (Joshua 6). The conquest continues with a series of battles against various Canaanite kings and cities, as God delivers the land into their hands.

Joshua 21:43-45 summarizes the fulfillment of God's promise: "So the LORD gave Israel all the land He had sworn to give their fathers, and they took possession of it and settled there. And the LORD gave them rest on every side, just as He had sworn to their fathers. Not one of their enemies withstood them, for the LORD delivered all their enemies into their hands. Not one of all the LORD’s good promises to the house of Israel failed; everything was fulfilled."

Theological Significance:
The entry into the Promised Land is a testament to God's faithfulness and the fulfillment of His promises. It serves as a symbol of divine providence and the importance of obedience and faith in God's plan. The land itself is seen as a gift from God, a place where the Israelites are to live according to His laws and commandments.

Covenant and Obedience:
The Israelites' possession of the land is conditional upon their obedience to God's commandments. This is emphasized in Deuteronomy 28, where blessings for obedience and curses for disobedience are outlined. The entry into the Promised Land is not just a physical journey but a spiritual one, calling the Israelites to live as a holy nation set apart for God's purposes.

Legacy:
The entry into the Promised Land establishes Israel as a nation and sets the stage for the subsequent history of the Israelites, including the period of the judges, the establishment of the monarchy, and the eventual division and exile. It remains a foundational event in Jewish and Christian theology, symbolizing God's faithfulness and the hope of entering into His rest.