This achievement can be done on the yellow ramps on the airport runway . Hit them on the side to start making barrel rolls.
Picture for reference:
I want to add one other detail that may save you a lot of time and effort.
The game registers your roll as a row as long as you hold the right trigger (accelerate). If you start making flips do not release the right trigger , hope that you will land or flip back on your wheels and repeat this process about 2 to 3 times. It will accumulate the rolls you made in the seperate jumps and you will get the Achievement.
It should be noted that one of the game updates is rumoured to cause some issues with the linking method. Although this is not confirmed and people have been able to obtain this achievement, using this method just fine after the updates have been downloaded it is worth mentioning that there is also a number of people that ran into some trouble. If this happens to you then you should go to your dashboard and clear your cache, using your system blade on your dashboard. Remove the update , start up your game again and don't download the update ( don't worry, you will be able to download it anytime when you log back in to xbox live) , now proceed as usual.