One of the first things we needed to teach our kids once they were able to walk was how to stay out of the street. We do a lot of walking, and having them know where it is and isn't safe to walk is really important. This was a bit more work up front compared to always holding their hands while walking, but has easily made up for that effort over time. Being able to relax knowing that they're going to stay safe on their own is really nice.

I started by staying close, and when approaching a street saying something like "we're coming to a street, time to hold hands." Then when crossing the street I'd say "we're holding hands because we're crossing the street." As they started to understand the pattern I'd ask questions like "what are we going to need to do when we get to the street?" and hear back "hold hands."

Once they had the pattern down pretty well, I started waiting to let them initiate the hand-holding in cases where that was safe. When coming up on a small street where I had good enough visibility to see that no cars were coming I'd wait and see what they did. If they reached up for my hand I'd praise them, while if they stepped into the street without taking hands I'd stop them, look surprised and firm, and correct them.

As they got this too, I'd start letting them get slightly ahead of me, again in the same cases where it was safe, so that now they actually needed to stop on their own. If they didn't stop, I could reach out and pick them up, and again tell them that they needed to hold hands.

I didn't keep notes at the time, but I think this took about 2-3 months of walks for each kid to go from having no idea that they needed to hold hands to me trusting them to run ahead and stop at the corner every time. I also don't completely remember when they learned it, but I think maybe just after they turned two?