If a king in ancient Israel wanted to declare war on another city he would ride into that city mounted on a horse or in a chariot. If that King wanted to enter another city in peace he would announce his intention by riding into that city upon a donkey. Four hundred years before Christ, the prophet Zechariah prophesied "Rejoicing greatly , O daughter of Zion. Shout, O daughter of Jerusalem. Behold, thy King cometh unto thee. He is just and having salvation; lowly, and riding upon an ass, and upon a colt, the foal of an ass." Jesus left the home of Mary and Martha on the first day of Passover to go into Jerusalem. Bethany is at the bottom of the Mount of Olives opposite from the side of the mountain that Jerusalem is on. This meant that in order to enter Jerusalem they had to climb to the top of the Mount of Olives and then go down the other side.
As Jesus and his disciples neared the top of the Mountain the road passed near by the town of Bethphage. As they came to the road that led to Bethphage Jesus stopped and asked his Apostles to go into the town and there they would find a donkey tied up and with it would be a colt that had never been ridden by man. They were to bring the colt to him. He told them if anyone asked they were to tell them that the "Master has need of it".
The Feast of Tabernacles is a time when the Jews would celebrate their acceptance of Jesus as their King. They did this by waving palm branches or branches with fruit on them and calling out the words "hallel" meaning "Praise" and "Yah" meaning "Jehovah". These two words came to be "Hallelujah" or "Praise to the Lord". When those with Jesus recognized the significance of the donkey they spontaneously lined the road to Jerusalem and waved palm branches calling out "Hosanna" meaning "save now" and "Hallelujah" meaning "praise to the Lord".
By this time with the many miracles Jesus had performed, not the least of which was the raising of Lazarus just a few days earlier, had spread throughout the land. He was famous. People had been watching for him and when they saw him coming they ran ahead to the let others know he was coming. The road was lined all the way into Jerusalem with people waving palm branches and throwing their cloaks and robes on the pathway before him. It must have been a very exciting time.
As they reached the summit of the mountain and began to descend into the Kidron valley the view of the Temple Mount must have been spectacular. The shouts of Hosanna and Hallelujah would have become even louder. Suddenly Jesus came to a halt and as he looked over the temple and the city of Jerusalem a sadness came over his face and tears to his eyes. His disciples must have wondered how things could go from jubilation and excitement to such sadness so quickly. Finally Jesus spoke and paraphrasing he said, "Oh Jerusalem, if only you knew what lay ahead for you, but you are blind and can not see it. The day will come when your enemies will surround you on all sides and destroy you so completely that not one stone will be left upon another." Finally he moved on towards the city and entered it through the Golden gate as a King.