I let my 5 year old son bike a few blocks ahead of me to get home. He stops at the roads and waits until there are no cars. It is a small town so if there is a car in sight he just waits until it is gone. He is a very sensible kid.
As far as wandering around with friends, I really have no idea. I wouldn't imagine it would be for another few years yet.
I let my 2 older boys (10 & 8) walk down to the local park or IGA together. I would not let the 8 yr old go on his own (although he did once with DH not far behind, but he made it to the IGA before DH caught up to him).
I also would not be comfortable with them going around with friends. I can trust them together but I don't think I can once others are added to the mix. Not yet anyway.
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