When do you stop watching your kids outside

I don't consider myself a helicopter mom, but I will watch them when they are outside. My boys do have a helicopter daddy, however. He wants me to watch them up close every second even in the house. I only recently convinced him I don't need to actually be with them when they are in view from our house at our neighbor's house as long as I occasionally look. But, I was wondering, I'll always worry about their safety, but at what point do I say let them go outside on their own and hang out with neighbor friends and be back at <insert time here> or when I call them in? They also like to be outside on their bikes. They are good about putting on their helmets and watching out for cars. I feel that I wouldn't be able to stop any big accident by being outside. I'd only be watching them get hurt up close. If anything goes wrong, they know to go to either me or one of the neighbor's houses in case of emergencies. When they are on their bikes, I will watch them closely since they are on wheels going fast, but DH wants me outside all the time. I have a health condition that makes it harder for me to be outside for long periods of time, but I don't want to boys to miss out of fun and exercise just because I have a health problem. I don't want to be the party pooper! DH is busy in the office so I can't really ask him to watch them. He's also tons more shy than I am, so even when he's not that busy working, he doesn't like to come outside if the neighbors are out too. Actually...make that, he won't come out. He does sometimes which is nice when he does.
 
They are 6 years old now. They are not responsible enough nor mature enough to have complete freedom, but when can I stop hovering as much as I or DH has been? I'm happy enough watching them, so this is just a curiosity and opinion question.

 

I guess it depends on where you live and factors as such. We live in te country with dh aunt as our neighbor across one field and his cousin a ditch and field over lol. So my main worries are driving bikes down our sloped driveway into traffic that is not much but drive like maniacs, and kid snatchers (one of many irrational fears).
That said, my kids will play out on the swing set or ride bikes in the driveway while I cook or fold clothes because I have a direct vision of them at all times. They know (Hannah I'm still leery on) not to follow toys into the road and they have to ask permission to go retrieve a toy by our pond (HUGE rational fear of mine!) and I will say they do great. We are also big into the tattle tale phase that I don't get anymore done with them playing outside vs inside -_-

 

It's a very safe neighborhood. I'm not worried about crime. I'd love for them to just use my driveway, but it's very slanted so they really can't ride their bikes on that. They'd have to be out on the street.

 

My girls play outside without supervision (I occasionally look out the window or go out and check on them).... They've been allowed to this for at least a year. For biking though, I'm out there with them. We live on a cul de sac and they ride on that, but I am out there watching for cars and warning them to get to the side. I'm not sure when I will let them ride outside without me.

 

The girls are 6 and Emmett is 2.5. We live on the main, fairly busy, boulevard of our neighborhood. Our front yard slopes down to the sidewalk, then there's the sidewalk, then another 10' (ish) of grass before the road. The girls are allowed to play in the front yard with the sidewalk as their boundary and ride their bikes up and down the sidewalk on our block (no crossing streets) unsupervised. I keep the front door and windows open and generally speaking can hear them all the time. If it gets quiet, I take a peek to see what's going on. I just call them when it's time to come in as they can't tell time yet so I can't tell them to be back by a certain time. All 3 kids play in the fenced in backyard by themselves, but I usually take a peek every few minutes unless I can clearly hear that all is well, just because Emmett is still pretty young. The biggest issue we run into is sibling arguments devolving into tears.

We often hang out at a friends place in the neighborhood who lives on a quiet street across from a playground. Her son (6) and my girls will cross the street and play in the playground on their own. We can see the playground from her living room where we'll often sit and visit while keeping on eye on our toddlers.

I'm hoping to start expanding their freedom more this year and would love if they could get themselves to and from school by the end of the school year.

 

My girls have been able to play in our backyard without me outside for a number of years.  It is not fenced, but they know that they have to stay back there.  And I peek out on them every once in a while.  I still don't really let them play in the front yard on their own.  Our road is not super busy, but it is often used as a cut through street for not so stellar drivers who drive too fast, and I just don't trust them being out there by themselves.  But we do not have sidewalks, and really the only thing they want to do out front (versus the backyard) is ride bikes or scooters in the street.
 
But we have been braving up this summer and we let our 12 year old neighbor/babysitter take them on bike rides around the neighborhood.  And we have also started letting them ride around the block by themselves.  It is hard on us! They are 8.

 

my kids have been playing outside without me for about 3 years now.  Its only this summer though that they can leave the yard and go across to the neighbors or ride their bikes/scooters.  They wear helmets and get out of the way of cars.  Abigail face planted off her scooter earlier this summer and broke her nose - me being outside wouldn't have stopped it, I just would have watched the carnage.
 
I feel if I don't give my kids some freedom they will never learn how to draw their own boundaries.

 

We live on a coffee farm.  The girls have been playing in the immediate house yard by themselves from about 3.  At around 4 I gave them slightly farther boundaries but not by much.  They are not allowed into the fields by themselves because wild pigs sometimes come down in the late afternoon.  They can kill a grown man.  There aren't any children their age living around here so there's really no reason for them to leave the farm without me. Its strange that my farm kids have less of a range than some urban/suburban kids.

 

We live on a cul-de-sac in a quiet neighborhood-my kids play outside with very little supervision (they are 6 and 9) I do know that all the neighbors look out for each other's kids and there is usually someone checking on them throughout the day/evening. 
Mine know the rules (helmets, watching for cars, dont talk to strangers, be respectful etc..) if they break these rules they lose freedoms until they can earn the trust back. 

 

If my kids are playing outback, I'll just peek out on them.  But we live on a fairly busy street with a corner that cars like to speed around (and people have had their parked cars hit in our neighborhood due to people taking the curve too fast) and if the kids are playing out front, we will be outside with them.  If we lived on a quieter street with little traffic, I'd let them play out front with less supervison.

 

Our street is pretty busy, so my girls do not go out front on their own. We do let them play in the backyard on their own, but will open the sliding glass door so we can hear them and also open all the blinds on that side of the house so we can frequently take a look for them. They are 8 1/2 now. They ride bikes on our sport court, but I would not have them riding out on the sidewalk or street in front of our house due to the traffic volume and disregard for speed limits.