The simple answer is that they probably didn’t. There were two groups of people. The Matthew account of the Triumphal Entry clearly delineates between the two.

It was a pilgrimage to Jerusalem.

Jesus began telling the disciples that He was going to Jerusalem to die months before this trip. The book of Matthew records three separate instances where Jesus told his closest followers of his plan to go to Jerusalem where He would be tried and crucified. The first was when they were in the far north near Caesarea Philippi (Matthew 16:21-23), the second was just after the transfiguration (Matthew 17:22-23), and the third was on the road as they traveled toward Jericho on their way to Jerusalem (Matthew 20:17-19).

The timing of this journey was significant. Jesus was going to Jerusalem for the Passover. Jews from all over the world were making this same trip at the same time. Jesus chose this timing on purpose. Any Jew listening to Matthew being read for the first time would recognize the significance of the timing and would be able to picture in their own minds the events as they unfolded.

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