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For us it's incredibly situation dependent. My 5 year old automatically holds hands, but if my hands are full I'm okay with her not. She knows to watch for cars and understands the rules.
But it also depends on where we are. The tiny parking lot for her sister's preschool? She doesn't need to hold my hand. A huge mall parking lot with god knows who is driving? She needs to hold me or my bag or arm or whatever. When the baby comes I'll be retraining both kids to hold the stroller (we haven't regularly brought a stroller with us in a good year now, so they're out of the habit) since my hands won't be free.
Both of my kids were probably about 6 or 7. I think it depends on the situation and the kid's ability to stick with you and pay attention to pedestrian and vehicle traffic patterns.
There are still some situations (downtown Washington, DC for instance) where I'll hold my 8 y/o's hand to cross a very busy intersection, or whatever.
Jelliebean1982:Most kids phase it out around 2nd grade. I see a lot of 1st graders wanting to hold hands, less of it in 2nd, and no one in the 3rd on up will hold an adult's hand. I am basing this purely on what I see as a teacher when we walk our kids to their cars at pick up time.
This is what I figured, and it's good to hear from a teacher's prospective. I don't want to scar them, but honestly, I will be sad when they quit.
Since I have 3 kids and 2 hands, usually, I am for sure holding my 2 year old. If its busy, I hold my 5 year olds hand and have him hold his sisters or the cart or something attached to us. If its no busy, I only hold the baby's hand. The amount of people/ busyness is all gauged in my head....
My 7 year doesn't usually put up a fight, more than likely its the 5 year old.
I will still sometimes ask my middle son (third grade) to hold my hand if the parking lot is busy, it's rainy or dark.
He cannot be seen behind many cars, as he is short.
Usually he does not take my hand, but I do sometimes ask him to. I like having LO, as it's an excuse to have him take LO's other hand. So, he's not being the little kid, he's "helping" me by taking LO's other hand.