Crossing the road is a serious responsibility. Parents spend a great deal of time training their youngsters on this particular skill. However, "readiness" is achieved in the normal way: teaching, lots of practice, testing. We can't rely on "self-report" - that is, your son telling you he is old enough is definitely not a good criteria. Instead, make sure you have taught him how to pause, look for cars to the left, the right, coming around the corner and so on. Then spend many days practicing with him. Then stand right behind him while he shows you how he can do it himself, again, for many days. You need to stand close enough to grab him in case he makes a mistake! Only when you see that he has a 100% accuracy rate should you let him cross alone. There is no room for error in this one. When you see that he never makes an error, no matter what time of day it is, no matter how many cars are coming, no matter how tired he is and so on, then you will feel confident enough to give him permission to cross independently.   Sarah Chana