I hiked the Appalachian Trail from the border of PA and NY to the end in Maine over about 2 months. In the beginning I was just listening to music, mostly calm relaxing stuff like Sufjan Stevens, Fleet Foxes, Explosions in the Sky or Godspeed You Black Emperor. After like a week of that I got bored and moved to walking with just the sounds of nature. That was nice for a while but got boring after like another week. Finally ended upon a good mixture of 1/3 podcasts (The Moth, The Bunker, This American Life, Welcome to Nightvale), 1/3 silence and 1/3 music like I listed before. If I was getting real tired I'd put on some heavier music like Run the Jewels or Rage Against the Machine