Mark makes it very clear that what happens in this passage takes place in Jericho, a city about 17 miles (27 km) northeast of Jerusalem, slightly west of the Jordan and somewhat north of the Dead Sea.  Jericho was a major city on the trade route between Mesopotamia and Egypt and was far more important in itself than Jerusalem was: Jerusalem, up in the mountains, was important only because it was the site of the Temple and consequently the home of the kings and so the administration of the country.  Jericho, though, did have a history of importance to the Jews: read the first 7 chapters of Joshua and 2 Kings 2:1-8. 

Here in Mark we see Jesus leaving the city surrounded by a crowd, and a blind man whom Mark names (which doesn't happen all that often in the miracle stories) has this interaction with Jesus.  The crowd at first tries to block his access to Jesus and then, at Jesus' command, encourages him to come forward.  

When the crowd changes and urges Bartimaeus forward, the beggar abandons his cloak.  That might seem minor, but we need to consider what this means.  Generally the cloak was, for the Jews, (1) almost a house and an identity, (2) protection, and therefore (3) a certain power.   We see some of this in the ideas of modesty and warmth and the roles that uniforms, religious garb, or even a beggar's rags can carry.  Look at what the cloak means in such passages as Exodus 22:25-26, Deuteronomy 25:13, Ruth 3:9, I Kings 19:19, and 2 Kings 2:8 and see what this abandonment meant. 

So Bartimaeus jumps up, comes to Jesus, and asks that he might see, and once Jesus heals him He tells Bartimaeus to “be on his way.”  This is the critical point: when Bartimaeus does see, he goes on without his cloak, and all that that means, to follow Jesus up the road.  “His way” is now to follow Jesus to Jerusalem and to the Passion. 

Note that something similar happens later in Mark when in the Garden of Gethsemane a nameless (and likely merely symbolic) young man “who followed Him had nothing on but a linen cloth.  They caught hold of him, but he left the cloth in their hands and ran away naked“ (14:51); this young man then reappears in the tomb on Easter morning (16:5).  The link is in the rather rare Greek word for “young man” used in the two places.

Bottom line: if we believe that we “see” who Jesus is and what He is about, are we willing to abandon all our little security and power, all the little things that give us identity and security?  Are we willing to follow Christ into His passion completely empty of ourselves and so be ready to enter into His Resurrected life?