Answer:
Chapter 1 - "The Alaska Highway"
"North to Alaska" by Johnny Horton
"The Wreck of the Edmund Fitzgerald" by Gordon Lightfoot
Chapter 2 - "The Stampede Trail"
"Going to California" by Led Zeppelin
"The Wanderer" by Dion
Chapter 3 - "Carthage"
"Simple Man" by Lynyrd Skynyrd
"Society" by Eddie Vedder
Chapter 4 - "Detrital Wash"
"Desperado" by Eagles
"Runaway Train" by Soul Asylum
Chapter 5 - "Bullhead City"
"The Gambler" by Kenny Rogers
"Badlands" by Bruce Springsteen
Chapter 6 - "Anza-Borrego"
"The Times They Are A-Changin'" by Bob Dylan
"Desolation Row" by Bob Dylan
Chapter 7 - "The Stampede Trail"
"Ramble On" by Led Zeppelin
"I'm Gonna Be (500 Miles)" by The Proclaimers
Chapter 8 - "Alaska"
"Wildfire" by Michael Martin Murphey
"The End" by The Doors