Why did Jesus send His disciples into town when He reached Jacob's well?
He sent them into town to buy food and to keep them away so they would not cause controversy, since Jews were not supposed to talk to a Samaritan. This left Him alone at Jacob's well to meet the woman of Samaria.
Les explains that Jesus foreknew what lay ahead as they traveled toward Galilee. Instead of circumventing Samaria as most Jews did, Jesus insisted on going through it. When He reached Jacob's well, He sent the disciples into town so they would not be around to cause controversy, because they were not supposed to talk to a Samaritan. He also sent them to buy food, as John 4:8 records. Jesus then sat on the well and waited. The woman of Samaria came to draw water, and though it seemed accidental, the Lord knew He would meet her. She came to recognize Him as the Messiah and ran into town to share.
(For his disciples were gone away unto the city to buy meat.)