With the help of friends, my little guy is learning to fly

In this week's poll question I asked at what age did you let your children start going places like the pool or the park with friends instead of a caregiver.
It's a simple question, but one that I am very curious about, because I have a child who is currently trying to flex his little wings and I'm having a hard time letting him fly.
I have written editorials before wondering if we have become a society who shelters our children and became a "backyard nation" where we isolate ourselves in our backyards with our privacy fences. Unlike a couple of decades ago when a residential neighborhood would be filled with children riding their bikes and adults hanging out on their front porches. Everyone looked after everyone else's young ones and parents felt confident in giving their children the chance to explore.
I believe that children need that opportunity for alone time, they need the chance to be able to venture out into the world on their own for some unscripted or scheduled play time. They need the chance to just be kids.
I also feel that as a society who is fed news on demand, as it happens, we see a lot of evil in the world. Evil has always been there and has been proven to not be happening in any larger amounts now then it was when I was a child. It's just more in our faces now when bad things happen. It's scary to read and hear some of the things we do, but in Mountain Home and other communities like ours, we are genuinely pretty safe. That's not me saying that nothing bad could happen here, because it can happen anywhere, at anytime, but I believe in this community and its big heart.
I believe all of these things and I believe that we need to go back to letting our children have more time where they aren't being told exactly what to do, when to do it and how to do it. But as a mom it is hard for me to let go and allow these things to happen.
This summer my beliefs are being tested. My family and I live very close to Carl Miller Park and the library and we are just a quick walk to the pool. My son is a very well behaved boy and hangs out in a group of other well behaved boys. The other boys are sons of our friends and all of them are a few years older then him. But he isn't just the tag-a-long little guy. They are all genuinely close to each other and are always disappointed if my son isn't with us or able to hang out with them. It isn't uncommon to find a pile of boys asleep in my basement, or on one of my friends living room floors ranging in age from 15 down to nine.
They are all big enough to head to the free lunch at the park or to the pool for afternoon swim on their own and this year they have convinced me that my little guy is ready to go with them. I can honestly say the first afternoon I turned him loose with his friends. I was so proud of him, yet I felt like I was going to vomit until I knew he was safely back at one of my friend's houses. I think I hit the tracking button on his little phone-watch that he wears, at least 20 times that day, but he arrived home unscathed and so happy.
I don't think him or I are ready for him to go out completely on his own, but I believe this first step of freedom was good for him and it was good for mom and dad too. I know if it wasn't for his group of friends though, he would still be sitting at a babysitter or being escorted to the pool by a grandparent and I think we are all perfectly fine with these little baby steps we've been taking.
I know that they are going to lead to him asking to take bigger steps, like walking home from school on his own, but that is a bridge we'll cross when we get to it. Right now I am just thankful that I can trust him and thankful to his group of friends that make it so I can let him fly a little while having his flock to keep an eye on him. We are lucky to have our son surrounded by such a good group of kids. They might all like to cause a little mischief, but it is always good natured. I am so thankful for those kids and for their parents that are helping us walk through this new phase as our son begins to venture out into the world on his own a bit more often.