This came up in a discussion about the terrorist trial in Boston, leading to a discussion of songs about Boston, further leading to the song Sweet Baby James:
Now the first of December was covered with snow
and so was the turnpike from Stockbridge to Boston.
Though the Berkshires seemed dreamlike on account of that frosting,
with ten miles behind me and ten thousand more to go.
This led to the OP–how many song lyrics rhyme the name of a city? We came up with “Little Green Apples” (And it don’t rain in Indianapolis in the summertime) and a twofer in Sinatra’s “Love’s Been Good to Me”
There was a girl in Denver
Before the summer storm
Oh, her eyes were tender
Oh, her arms were warm
There was a girl in Portland
Before the winter chill
We used to go a-courtin’
Along October hill
That covers Massachusetts, Indiana, Colorado and either Maine or Oregon.
Steely Dan, “My Old School.” You get a triple helping of Annandale, and one California for dessert:
…
I remember the thirty-five sweet goodbyes
When you put me on the Wolverine Up to Annandale
It was still September, When your daddy was quite surprised
To find you with the working girls in the county jail
Oleanders growing outside her door
Soon they’re gonna be in bloom Up in Annandale
I can’t stand her Doing what she did before
Living like a gypsy queen In a fairy tale
California tumbles into the sea
That’ll be the day I go Back to Annandale
Tried to warn you About Chino and Daddy Gee
But I can’t seem to get to you Through the U.S. Mail
Shuffle Off to Buffalo:
“To Niagara in the sleeper
There’s no honeymoon that’s cheaper
And the train goes slow.
Oh, Oh, Oh
Off we’re gonna shuffle
Shuffle off to Buffalo.”
Honeymoon Hotel (Hollywood):
Hotel Detectives: Girls, you’ll have to scatter.
Girls: We don’t see why we should.
Detectives: You’re in Jersey City/And not in Hollywood!
I didn’t think I’d find a match for Connecticut, but here are the lyrics for “Connecticut’s For Fucking” by Jesus H Christ and The Four Hornsmen of the Apocalypse. (The idea is that the state is so boring that that’s all there is to do.) The lyricist rhymes Old Lyme with “all the time”. More impressively, he rhymes Lake Quassapaug (admittedly not a town or city name) with “catching frogs”.