Item description:

1 - Pole Position: Complete & win 3 Go-Kart Street Races. 2/3 are done, the last one is with the townies.

This area is last to be unlocked in the game which is why I saved this trophy for till post-game. Now, you will load in the docks save area, which is the one closest to the carnival. The trophy icon on the map in the screenshot is where you need to go. You need to travel to the townies location in the photo, & that is the last race. You need to win, or else you will not earn the trophy.

Here is a YouTube video by Snickel:
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