Wrestling with this question as well. Mine are 10,8, and 6. The 8yo has been allowed to ride to his friend's house 1/3mi away and can ride himself back. Him and his friend has some reign on riding to the school and the neighborhood between our house, his house and the school when they're both together. My 10yo is permitted to ride around the blocks connected to our road but she doesn't have friends in the neighborhood she can ride to. Her closest friend requires walking through the back yard, the next is well past the school over a mile away and I'm not comfortable with her soloing it. For next year, if they go to school, they are considering wanting to stay homeschooled, I would ride with them to school half way, there's a sketchy street they people run the stop sign at in the morning. Once past there they can finish alone. We have to sign something with the school, which they don't like, that says that the kids can ride home and leave together without a parent. My oldest really wants this and I think wants to go back to school. The MC prefers homeschool and the youngest doesn't know what he wants. If just her, I'd have to go with her but it might be her and her friend riding together.
Don't know how my parents were so cavalier with me riding 2-8 miles away on any given day with no concern for where I was at 5, but the level of common sense my kids display freaks me out.