Are there enough relevant songs to travel on a road?

[hotdogPi]

Imagine that you're driving on I-90 from Boston to the New York state border and beyond.

• Songs about Boston (or by the band Boston) make sense until about Worcester
• No idea for (most of) Worcester to the Quabbin Reservoir. Any ideas?
• Approaching I-84: One of the many New York City songs. You're not actually going to NYC, so it won't be wasted. (Musical settings of The Road Not Taken would be reserved for much more rural junctions.)
• Near the Quabbin Reservoir: a song about a ghost town?
• Palmer, MA: Golf? Yes, I know the town isn't named after the golfer.
• Wilbraham, MA: Ice cream? It's Friendly's headquarters.
• Air Force theme song for Westover Air Reserve Base
• Springfield, MA: Simpsons theme song
• Songs about a theme park, as you're near Six Flags New England. You can probably get more than one song here.
• Alice's Restaurant – 18 minutes. You might have to shift this a bit east, as the relevant section of I-90 overlaps the relevant section of I-90 for Tanglewood.
• Something by the Boston Symphony Orchestra in Tanglewood. It should be long enough so that everything between Six Flags and the NY state line is covered.
  
• America by Simon and Garfunkel explicitly mentions both termini of the Mass Pike, so it can be used right before crossing the border.

Once you get into New York, I have no idea. The Erie Canal should definitely be one of them. There are a decent number of town and village names that are names of famous cities in other countries or the countries themselves, but even two songs per unusual town name won't last you 300 miles. Cooperstown is a bit far from I-90; Take Me Out to the Ball Game (yes, it's more than 30 seconds long) should probably be played when right next to a baseball stadium instead. I'm not sure if any Native American reservations pass through or near I-90. University school songs when you pass by them could be a possibility, but would people be interested?

Now, if you were doing I-10 in the Southwest, you could have country/western songs all day.

Then you have the songs that work in many places: the state capital song (although it's a kids' song), I Can't Drive 55, etc. I figure if radio stations can play the same song twice six hours apart, you wouldn't be limited to using each song once on a cross-country trip.

[thspfc]

I-43 in Wisconsin could be entirely filled with Packers songs, as I-43 is the unofficial Green Bay Packers Highway.

[jp the roadgeek]

Imagine that you're driving on I-90 from Boston to the New York state border and beyond.

[/li]
• America by Simon and Garfunkel explicitly mentions both termini of the Mass Pike, so it can be used right before crossing the border.

I think you mean Sweet Baby James by James Taylor (although the Pike ends in West  Stockbridge and he only mentions plain Stockbridge).  America refers to the New Jersey Turnpike (although the Yes version would take up a good chunk of your drive between Westfield and Lee)

[TheHighwayMan3561]

Highway 61 Revisited works in a literal sense for Minnesota these days, since it was officially broken apart by I-35 i30 years ago.

I'm not that familiar with Atmosphere, but there are plenty of songs about Minneapolis. The one I can think of is "Always Coming Back Home to You"  that mentions Lyndale Avenue. The "Say Shh"  hidden track on that song talks about coming home to Minneapolis, and  also includes a roll call of Midwestern cities at the end.

[Henry]

If you're driving to the Windy City, then a playlist full of Chicago-related songs (e.g. Sweet Home Chicago, and taking into account the many artists who are based there) makes the most sense. Bonus points go to music made by the band Chicago.

[webny99]

I'm not sure if any Native American reservations pass through or near I-90.

There's the famous one southwest of Buffalo that's been discussed a lot here on the forum due to the longstanding dispute between the state and the Senecas. The resulting horrific pavement quality was finally being fixed as of last fall.