The Road to Jerusalem was a week-long walk from Jesus' HQ in the fishing village of Capernaum on north shore of the Sea of Galilee. That's where he spent most of his time.
The people there were welcoming and accommodating, compared to the Jewish scholars in Jerusalem. Jesus reportedly healed a wide range of illnesses and diseases. And he was known to feed the crowds a few times.
But Jesus did go to Jerusalem for some of the Jewish festivals, including the biggest one: Passover. He spent time teaching in the Temple and revealing the hypocrisy and selfish egos of many Jewish experts in the Laws of Moses and the commentary by rabbis from decades and centuries earlier.
South to Jerusalem
The Road to Jerusalem led south of Capernaum. But Bible writers usually described Jerusalem as “up” from everywhere because it sat on the ridge of a hill. People had to climb to get to Jerusalem. There was also, perhaps, a sense of reverence in the description of going up to what became known as the Holy City. In the other three Gospels, the story of Jesus chasing the merchants out of the Temple shows up in the final days of Jesus’s ministry (Matthew 21:10-17; Mark 11:15-19; Luke 19:45-46).
Passover, the big holiday
Jews call this holiday by its Hebrew name: Pesach (PAY-sah). It was also called the Festival of Unleavened Bread. This bread was flatbread made with no yeast. Yeast is what makes bread dough rise. Many Jews today celebrate the holiday by eating cracker-like matzo. Tortillas would also qualify. The festival is a seven-day celebration beginning on the 14th day of the first month in the Jewish new year: Nisan, usually sometime in March or April. It varies because the Jewish calendar is based on the cycles of the moon.
Jewish pilgrims traveled the Road to Jerusalem, coming from all over the world to celebrate Passover in Jerusalem, somewhat like Christian pilgrims today go to Bethlehem at Christmas and Jerusalem at Easter. One difference is that the pilgrimage is optional for Christians, but the law of Moses ordered it for Jews. At Passover, Jerusalem swelled to many times its normal size.