I didn't have my own route but helped a buddy who had a long rural route. This was back in the early '50s, lots of farm houses, rolling hills and wide open spaces. No "roof shots" or "porch skippers" for us...all deliveries were made to rural paper boxes located near the customers long country driveways.
Of course our bikes were the old heavy cruiser types that everyone had. For some reason I remember the 26 inch fat US Royal tires with the "figure eight" tread pattern that many of those bikes seemed to use. My bike was made up mostly of old junk parts with a Whizzer motorbike front wheel that I was extremely proud of.
We had one customer who lived at the end of a long dead end road who was a mean old hermit type that we would sometimes torment. Occasionally we would fold his paper extra tight into a small package and push it tightly, far into the box. Then for the finishing touch to our handywork we would cram ice and snow into the box until it was full. This mess, of course, would usually freeze solid after about an hour.
Don't know how he managed to get these "special deliveries" out of the box, but the word BLOWTORCH comes to mind. I don't recall that the poor old guy ever complained or reported us to the newspaper.
People weren't so quick to react in those days.
Good thing.