I ride on the rails to trails thing a lot.
Not sure if you have it in your area but basically they paved a few hundred miles of old railroad tracks. Some areas are mostly wooded, a couple industrial spots.
I always listen to music, both ear buds in because it's a fucking paved railroad track.
If I'm riding on the road I only ever use 1 ear bud and keep the music kind of low. Riding in traffic or heavily populated locations without being to hear is bad. The best stretch is from Oregonia,Ohio south to Milford. All wooded and follows the Little Miami river very closely.
>http://www.miamivalleytrails.org/little-miami-scenic-trailIt's actually longer than the link says. I did 60 miles in 3 hours once.
As for etiquette:
1. let people pass you if they're faster.
2. if you are stopped move off the trail completely.
3. if you are coming up behind someone yell, "on your left"
4. if you are passing someone who is going the other direction, just don't hit them. A nod is polite but no required.
>tl:dr stay out the way, don't startle people. 