Good for you for taking pictures! Keep documenting the damage, and if possible, get pictures of trucks with the contractor's logo on the side. Any time you see something like this starting to happen, it's great if you can quickly get some "before" pictures so you can prove the extent of the damage done by that activity.
This is the reason we added a clause to our bylaws saying that if anyone causes damage to the road beyond normal wear and tear, they are responsible for the cost of repairs. Check your bylaws and see if they include any such clause. If not, you may still be able to take it to Small Claims Court.
But before you go there, I'd try approaching the contractor in as friendly a manner as possible, point out the damage, and ask politely if he has plans to repair the damage. Try not to get confrontational, as some people have every intent of making things right until someone accuses them, and then they go whole hog in the other direction. So start by giving him the benefit of the doubt.