These two verses seems to be a picture of some sort of a pilgrimage, either a religious pilgrimage, or of a farming community perhaps gathering their produce and going up to the city to sell it. Wisdom stands at the high places, the mountain passes, which all travellers must use.
As you set out on life's journey you come into youth and you look at the great scenes, the hills, the mountains, and the skies, and isn't it true that for everyone there is an awareness that God is behind these things, and the only real understanding of great and high things has to do with the Lord. The need for divine information and divine shrewdness comes to us in the very early stages of life. That is how we account for things we don't understand and we have a kind of respect for the things of God.
Then you come to junctions and cross-roads – worrying and disturbing, great decisions – and you are aware so often because you feel humbled that you have a need of divine knowledge, and you need God to help you. Then you come into the stage of life where you are going to be launched out into a more complex existence into the city stage, as it were, the adult stage, among many people. Again, there are times when it is obvious that you cannot be on your own and there is more to this life than just what you can get and what you can have. In the case of everyone there is this instinct and this need for some understanding of truth. But it is brushed aside.
Wisdom is sounded out in courts of government, it is sounded out in royal palaces, it is sounded out by trades people on journeys, and it is sounded out at the crossroads, the great places of decision in life. So in all levels of society, all people and at all times, there will be moments of disquiet, a longing for a better and a deeper explanation for life and living, the sounding of conscience and the message of the gospel in clear form going out among society.