Hey Goblinchief - this is a really good question, and one that I lived through with my two kids. When they were tiny, they rode in the bike seat behind me; when they were four to seven-ish, they road on the back of a tandem (we had a kid-adjuster to make the pedals reachable for their tiny little legs.) These steps were simple questions of transportation. But it wasn't until they were on their own bikes that their real education began, and it took YEARS of me riding behind them, more or less protectively, depending on the conditions, always explaining what to watch out for (how to handle this sort of intersection, "watch that car ahead, he looks like he's going to make a right turn in front of us," "see that grate with the parallel bars open; if you get your tire in there you will go flying off" "watch that loose gravel on the edge of the road there" etc.etc.) We rode in all conditions, in all times of year (Pennsylvania hills and winters), short trips so they could learn how to ride to their schools, longer trips to get places we wanted to go, summers we did week-long touring rides just for the fun of it. It took years, to teach them as well as I could. And it worked. They understood that biking safely took a lot of attention. They saw me take it seriously, and they took it seriously, too. Sure there were some roads I wouldn't take them on. But I often took them on roads that were a little beyond my comfort zone (though maybe we'd start on a Sunday morning when things were quieter, til they got the hang of it) and eventually, they became highly skilled riders. When they reached the age when they could get their drivers' licenses, we offered each of them the same deal.... put off driving for a few years, and we'll buy you a brand new touring bike. (Both of them took the deal.) Now that they are adults, living independently in different parts of the country, though both got their drivers' licenses, both rely heavily on bicycles for their transportation, and this is to me the greatest indicator that all those nerve-wracking years of riding behind them and explaining the rules of the road, were worth it. I encourage you to exercise your best judgment, don't be afraid to push a little past your comfort zone, as long as they can be safe on the roads you're taking them on, and utilize every opportunity to teach them how to ride safely. My one kid was road ready at about six; the other, though able to ride a two wheeler at age three, was far too distractable and too much of a dare devil, so we went slower with that one. Enjoy the ride!