How much freedom to give preteen

[Isolatedandfrustrated]

I know that everyone will have different opinions on this and there are lots of factors involved but I'm interested in to see what other parents allow.
My son is 11, in yr6 of primary. He starts secondary school in September so I'm wanting to give him more independence because of that.

We live on a nice housing estate in a nice area. There are hardly any kids on our estate but luckily his best friend lives in the next cul de sac. I have allowed him to go out and play with his friend since he was about 7 years old. He's very street wise and sensible. They've always played football, hung out in friends cul de sac or occasionally biked round the estate. He'd go out most nights after school until 6 when it's our tea time.
These past few months him and his friend have been venturing further. Asked if they could go to local shop, no problem. But of course at that age he now wants to go further and further. The roads are very busy around here, especially at tea time. There is a local field /play area just off the estate across a very busy road. They started going there, without telling us.
Now I find out theyve been going pretty far in all directions, just roaming around really. I can see his location on Google family link, and he has his phone with him. I've told him to tell me where he is going. Trouble is I don't know what's acceptable at this age. I'm quite a scaredy cat type of person. I didn't go out at all until I was about 15. He's the opposite to me and wants to be out all the time. To be truthful I am not comfortable with him going as far as he is and going to this park where there are always teenagers having around it.im terrified he's going to get robbed, bullies, beaten up or have an accident. But I know I have to let him spread his wings.
I have a daughter who's 8. There are no other girls on our estate at all so she never plays out and never will until much older. (she has playdates etc). This makes me feel guilty because I have one out constantly and one who never can through no fault of her own.
I feel like he's never happy with what I allow and is always pushing for more, to go further, to stay later etc which is natural of course but I just don't know what is right at this age. Any advice?

I think this really depends on your local area.
My daughter is also in yr6 but she doesn't have any friends living very close by. We started about a year ago, I would drop her to the park closest to her school and where her friends live, then pick her up at a specified time. This developed to meeting her friends in town with me (then I'd sit in a Costa while they shopped) then later dropping her at her friends and they would walk into town together - this is about a 10-15 minute walk. Town has traffic but plenty of safe crossings, other roads are fairly quiet. We've just moved onto walking into town herself to meet her friends there (still a 10 minute walk just on her own).
In September she needs to walk a similar distance on her own to school, although there are plenty of other kids walking in the same direction including her big brother.

In regards to your DS I think you need a compromise. Think realistically about the skills he will need to develop before September, while also weighing up actual dangers that come with your area. I would also discuss with your DS your expectations i.e. knowing where he is going in advance.
Fwiw I have personally found that the barriers get pushed more and more from this age. My DS is 13 and goes all over town by himself now. He even has a paper round so out every morning before most people are out of bed. The next step is always nerve wrecking but I've kind of got used to my nerves being fried so it's slightly easier now somehow 🙈

I think it's fantastic he Wants to be out. So much better than stuck indoors
I have a very similar dynamic with my son and daughter...son always out with a gang of boys along football but my daughter doesn't have the chance for autonomy as no friends on our street.

Re..your daughter. Could you arrange with a mum friend to set up some situations where her and a friend do some more autonomous little trips out