Great Topic. I could this for a while too, but I'll throw out a couple of highlights from when I was a growing up:
Fleetwood Mac - "Rumors" and John Stewart (notice the spelling, not that Jon Stewart) - "California Bloodlines" and "The Phoenix Concerts" will always remind me of the family summer drives to Oregon in the motorhome in the late 70's early 80's.
Lynyrd Skynyrd - "One More ^ From the Road" will always remind me of my drunken dad late at night in Orange County doing air guitar until my mom yelled from the top of the stairs to turn it down, which he did, until the 11 minute version of Free Bird came on, and the volume knob went through the roof. Always a silent morning after that, and you could feel the tension. Good times.
U2's The Joshua Tree will always remind me of the drive through central CA on the way to Mammoth.
Van Morrison's "Moondance" will always remind me of a train ride from Cork to Dublin when I was leaving Ireland, moving back to the states.
A couple more recent examples, any Jimmy Buffet reminds of a girl I dated who's family had a boat in Crisfield, MD.
And, like Pollard, The Postal Service will always remind me of the winter in DC.