This summer is a whole new world for me - having a somewhat mobile 14 year old - out of school for the whole summer. Setting a curfew and biking boundaries has never been an issue in the past, before this year, if he wasn't home he was at his best friends house down the street.
We live in a large housing plan neighborhood, which is up a long hill about 1 mile long, and about 2 miles away from the center of our small suburban town & shopping district.
Suddenly this summer, he has a ton of new friends in the neighborhood, whose parents let them ride their bikes anywhere, and let them stay out until 11:00 every night. DS thinks I am being "over-protective" because I said he has to be in by 10:30 on weeknights, and 11:00 on weekends, and he is not allowed to be on his bike outside of the neighborhood after dark.
So far, complaints and all, he is abiding, but we have a lot of summer left! I can't believe I was not prepared for this! DH and I both grew up a little further up this same hill. I can remember NEVER being allowed to ride my bike on the main road down to town... I still agree with my teenage self that my parents were way over-protective not letting me when everyone else could.

Of course, my parents think we are nuts letting DS ride his bike down to the community pool with his friends!