I had a couple of morning routes (Detroit Free Press, the lib paper) with about 150 houses to deliver to, and a couple of afternoon routes (Detroit News, the good paper) with another 70 or so houses to deliver to. Had the saddle bags on the back of my bike, another bag on the handlebars. Had to put each one either in the mailbox on the front of the house, or between the storm/screen door and front door... rain, snow, or shine. Sucked in the snow, and to this day, my definition of "cold" is "does your snot freeze in your nose?" Had to ride your bike to the paper station (for Detroit News) or drop off spot (Free Press) in your area to pick up the papers, then ride to your route. Thanksgiving Day paper was by far the biggest/worst. Collecting every week (I'd try to get people to do it every two weeks or even a month at a time) sucked...
But it was a big part of who I am today, and stuff like that doesn't exist for kids anymore.
Other big memory? Trying to find someone to do my paper route(s) in the summer when we'd go to my grandparents in Canada... Would draw maps on paper showing every house on every block and identifying which houses to deliver to.