A direct route to the promised land would have only taken 10 days, not 40 years. Why send the people through the wilderness, then? God wanted to both A) humble, and B) test his people. Would they be loyal to him or not? He does the same with us today.

Exodus: Bought With A Price
28:14

The Exodus Series: The Death of the Firstborn and the Escape From Egypt
28:00

The Exodus Series: The Most Ancient Catechism
27:44