I don't understand why a person would be bored riding by themselves. There is so much to think about ... work, school, family, friends, the scenery, the people in shop I stop in to get some food, distant future plans, the things I need to do in the near future, etc. etc. etc. etc.

My longest solo ride was 600 km ... a 600 km randonnee back in Alberta in 2007. I did have music for the first 7 hours of that, but then I got tired of the radio and did the rest of the ride with my own thoughts.

The story of that 600K: http://www.machka.net/2007/2007_600_RedDeer.htm