During the days of Jesus' life, devout Jewish men would make three pilgrimages to the Holy City each year for the major festivals of Passover, Pentecost, and Tabernacles. Jesus and his disciples would set out on pilgrimages together, 120 miles one way from Nazareth to Jerusalem. The most direct route to Jerusalem would be through Samaria, a dry, barren, hot landscape, with heavy crime and cultural tensions. Adding as much as 30 miles to their pilgrimage, Galilean Jews would avoid the difficulty of Samaria and stay alongside the Eastern banks of the Jordan River.
Though required by law, it was seen as a joy to journey to the Holy City as one of God's faithful people. Along the way, God’s people would walk in a prayerful and worshipful way, reciting and singing the Songs of Ascent.
Jericho, the “City of Palm Trees,” was considered a pleasant and desirable place with a warm winter climate and several sources of fresh water. Waiting in the path of Jesus and his disciples as they woke up on the last day of their journey was Bartimaeus, a beggar looking for spare change. With the dust of traveler's feet on his lips, he would watch the wealthy come and go. While all the people passing him were affluent enough to go on pilgrimage, he was stuck on a beggar's mat.
The annual pilgrimages were a rhythm of life for God's ancient people. They would stay close to familiar landmarks and travel with people they knew. In the midst of the arduous climb towards Jerusalem, they would cling to their Scriptures, recognizing the need for God's help and deliverance.
Are we any different today?
A pilgrimage is any time in life when we are trying to get somewhere while staying focused on God. Our destinations are often things like a job, a financial provision, a relationship, a healing, or a reconciliation. But we cannot control our pilgrimage towards any destination any more than those around Jesus could control their pilgrimage towards Jerusalem.
All the people around Jesus are on pilgrimage to meet with God, but God is already there! Jesus is the one who controls our pilgrimage - like he did for Bartimaeus, God can insert Himself at any moment, whether we are comforted by the illusion that we control our lives or discomforted by the reality that we don't.