I am a classical musician and also have a pendant for the older, golden-aged songs and music. Actually, I like all kinds of music but gravitate more often to:
My favorite train song is "On the Atchison, Topeka and the Santa Fe." It was introduced to us by Judy Garland and company in the movie "The Harvey Girls," a movie about the waitresses who worked Santa Fe's Harvey Houses. I like the song because both the music (melodies and rhythms) and the lyrics talk about riding the train, the rhythms of the train, of wanting to be on that train,going to whereever it was going. This same song has been used in several MGM cartoons--especially "Tom and Jerry" cartoons, especially when a train was involved.
Another Judy Garland introduced song is also a favorite: "The Trolley Song" from "Meet Me in St. Louis." To me, it works just as well as a mainline train song as it does as a trolley song.
I also liked the theme song to "Petticoat Junction" with its trainlike rhythms and, of course, showing the Cannonball riding through the countryside.
"Wabash Cannonball," "Freight Train," "Orange Blossom Special," and "City of New Orleans" are also good, favorite train songs. It's interesting to note how many of the "good" train songs are in the country/bluegrass genre. But there are good train songs in other genres: "Midnight Train to Georgia" by Gladys Knight and the Pips is an example. I also like (still) Sheena Easton's "Morning Train."
There are a lot of American folk songs about trains (or that were originally songs about trains): "I've Been Workin' on the Railroad," Ballads of "John Henry" and "Casey Jones," "500 Miles," and "She'll Be Coming around the Mountain."
The classical afficianado in me also likes to CDs that I have: Locomotive Music 1 and 2. These are classical (light-classical) compositions that have to do with trains. During the 19th century, when the railroads were being built in Europe, composers (like the Strausses) were often asked to write waltzes, polkas, or other types of works to celebrate the opening of a new line and/or railroad stations. Sometimes the music was very descriptive of the train: steam puffing, starting slow and gradually accelerating up to speed ("The Acceleration Waltz"), the pleasure of the ride from place to place, etc. This music was written by a wide range of composers (from various countries), and it seems that polkas and quadrilles (like rhythms of a horse) work best at representing the rhythms of the train. And sometimes, the compositions have no real connection to the train; they are just nice pieces of music. One waltz--"The Steam Waltz"--actually refers to a coffee maker of the time, but it also works in describing a steam locomotive. Arthur Honneger wrote a piece entitled "Pacific 231" (the European way of designating steam locomotives; in the USA, a Pacific would be designated as 4-6-2) is descriptive of not only of a steam locomotive but of the entire mechanized world. Supposedly, Gershwin's "Rhapsody in Blue" was in part inspired by the sounds and rhythms of a train (in "Fantasia 2000," the piece was accompanied by scenes of NYC including a subway train).
Classical composers Dvorak and Ravel were both train lovers. Supposedly, the last movement of the "New World" symphony (#9) mimicks the sound of a train accelerating up to speed. Steve Reich wrote "Different Trains" and tells of a sadder aspect of trains, using trains to take thousands(plus) of Jews and other prisoners to concentration camps.
Though not directly about trains, Wagner's "Ride of the Valkyries" is a piece as much about movement, especially flight (like the helicopter battle scenes in "Appocalypse Now"), and works just as well to represent the speed of a train. I've actually listened to it while on a moving train, and it works.
Of course, there are a lot of things I listen to that have no specific reference to trains; they are just nice pieces of music. Sometimes I like to listen to music that is about (mimics) nature, representing the nature outside the train window. Such pieces include: Beethoven's "Pastorale" Symphony (a day in the country), Smetana's "The Moldau (Vltava)," which depicts the course of the river through the Czech countryside and through the city of Prague, Strauss' "Blue Danube Waltz," Debussy's "La Mer" (the sea), anything from Wagner's Ring Cycle (as the Valkyries, above)--a lot of it has to do with the Rhine River.
One time I was on the Starlight starting the climb over the Oregon Cascades (out of Eugene), "Star Trek: The First Contact" started with its lovely stringed score (music by Jerry Goldsmith) for the opening credits. i am a sucker for lovely string melodies and thought it complemented well the mountainous scenery outside my window.
Edvard Grieg's music is evocative of his native Norway. When I listen to his music (ie, "Peer Gynt," and the Piano Concerto in A minor) I can image a panoramic scene(s). It's easy for me to transfer thoughts (and pictures) of the European landmarks and places to scenes here in America. With Grieg, I associate his music with here in the Pacific Northwest, especially of the Puget Sound/Seattle areas. And of course, there are a number of great, pastorale works by American composers that I like: Copland's "Appalachian Spring" and "Rodeo" and Grofe's "Grand Canyon Suite." I also have a CD called "Roundup," which has music from western movies and TV shows that work nicely to complement the wide-open spaces outside my window on the Starlight, Builder, California Zephyr, Sunset, Southwest Chief, (before they were cancelled) Desert Wind, Pioneer, and North Coast Hiawatha.
On the Coast Starlight in southern California, I can image hearing Beach Boy songs "California Girls" and "Surfin' USA" and such.