I went into my Checkpoint blue print and created couple of components, a root, an arrow a trigger and a particle system, I've also incresed the scale of the trigger box as it will be my checkpoint so it needs to be good size so the player can pass through it with ease. The arrow component has been added so the player can only pass the checkpoint through the front of them (if the player passes the checkpoint backwards it will not count)

Inside my checkpoint blueprint I created a blueprint function, the checkpoint system which will be cleared when overlapping ends. So the checkpoint will disappear after the player has passed through it.

I went ahead and fixed my checkpoint asset so it now appears connected to the road unlike it did before. I have accomplished this by changing the asset from a door asset which didn't have the bottom pillar to a window asset which has one.