Great train trips in the US: "City of New Orleans" as an inspirational song

The only long-haul (non-commuter) train trip I ever took was in 1988 from Newark to Savannah for Thanksgiving with my then-fiance to be with the future in-laws. What I recall about it was seeing the back end of countless poor rural towns in the mid-Atlantic and South. It was an eye-opener for me because I was accustomed to either Cupcake Land (defined as prosperous homogeneous small-medium cities in Minnesota in the 70s-80s, or wealthy NJ suburbs) or urban cityscapes in the NE, nothing in between.