Oh yeah, we did that too, we called it “skitching”. They wouldn’t plow the sidestreets, so if we got at least 6 inches of snow, it was game on!
In the summer, we would wait for the ice cream truck to come around, and get some kids to run out so he would pull over, then a few of us would sneak on the rear bumper and see how long we could ride before he noticed us and chased us off. Sometimes we would end up like 6 blocks away and had to walk home.
I remember my parents going out for the day ans leaving us money to go to McDonald's or wherever on our bikes. If we could get others to chip in we would go get pizza.