I never learned to ride my bike with no hands when I was a kid.
I'm not sure if this was because it scared me - it did - or because I wasn't the most coordinated of children - I wasn't - or because I grew up riding bikes on bumpy, sandy dirt roads in Liberia - I did - but I just never could let go with the second hand.
One hand, fine. I could do one hand. Two was just scary.
It wasn't until the summer after college, or maybe the summer after law school, some summer when I was living in the basement of my parents' current house, that I learned to ride no-handed.
My parents' neighborhood is full of flat streets with very few cars. It is basically perfect for riding a bike no-handed, and whichever summer it was, I finally learned to let go of both handlebars.
But now that I use my bike for commuting, I have a milk crate attached to the back of it. The milk crate is full of books (heavy) and a gi (heavy) and my daily snacks (heavy), and so the bike is more top-heavy that it would otherwise be. That, and I'm always riding next to cars, so letting go of the handlebars seems ill-considered.
Today I rode my bike home from bjj, 32 blocks down our beautiful street (we live on a bike route street and my martial arts studio is two blocks off it), and I found myself, despite the top-heavy milk crate, sitting back and letting go of the handlebars and reveling in the letting go.