Love the concept and the vibe! Super cool Americana feeling.
I struggled a bit with the rules. Once I missed a single checkpoint I was sort of stuck racing without progressing at all. So then I started driving really slowly to help keep between the checkpoints. The risk of missing a checkpoint, given the wide turning circle, was too great.
The check points also don't follow the road, which means I had no idea where the next checkpoint will be, so I couldn't go fast because the checkpoint might require me to take a corner sharply.
I think I could really love this game if the level design helped me feel like a badass. It's such a cool theme for a racing game!