And yet, the road also can provoke anxiety: We take the road, but it also takes us. Will we survive the upcoming hairpin turn? Are we on an extended detour, full of delusions? Do we need to turn onto a new road?
Wyatt and Billy are on the road, but they don't have to be. They had at least two chances to stop somewhere and find a home. That's where those last two questions and Wyatt's statement come in. He is saying that they blew their chance, the took the extended detour and didn't turn onto the new road when they should have and well, look what happened. They didn't stay where they could have been accepted and continued to poke at society right in people's faces and that got their friend killed and in the end them killed as well. When they are at the farm Wyatt looks like he might consider that to be a nice life once he got older and when they were with the hippies he seemed like he might want to settle down and stay there right then. But they kept moving and went from places where the people were friendly to them to places where the people hated them. They blew it by leaving where they could be accepted, whether they fit in or not.
The culture and counterculture also blew it. They were both too extreme. The counterculture, like Billy and Wyatt, were so very different from the mainstream culture and refused to make concessions, simply expected everyone else to accept them. When they are in the diner in the small town and simply sitting there waiting for service is a very good example of this. The mainstream culture was also too extreme but in the other direction. It is too traditional and too unchanging. The girls in that diner who were so desperate for Wyatt, Billy and George wanted something new and different and the culture that they were part of restricted them from it. The fact that a counterculture so extreme and different grew out of the mainstream culture says a lot in itself about how much too traditional the mainstream culture was. In short they all blew it because a middle ground needed to be found and both culture and counterculture needed to make concessions for the other but neither would and so they will both destroy each other and themselves.