Great question!
My first Amtrak ride was a trip on the Lake Shore Limited in Dec. 1995 from Boston to Chicago with my husband, who was my then new boyfriend. I hadn't been on a train since I was a little girl (taking the train between Cincinnati and Bowling Green in the 1960s) and I don't recall much of those days.
But the trip to Chicago on the LSL I remember. I was in graduate school at the time and I had come to Boston to visit my husband. Upon arriving, I got a nasty cold which I gave to him and we both were very sick. One of his neighbors took pity on us and brought us homemade chicken noodle soup and other food because we were too sick to get out of bed.
When we did finally recouperate, we decided we were going to go do something grand -- and that something turned into a trip to Chicago on the Lakeshore Limited. My husband told me all about the sleeping cars he remembered as a kid so we were both expecting those types, so you can imagine our surprise when we had the Viewliners!
They were fantastic and I really think -- no, I know -- that was when I fell in love with train travel. Everything was great. The service was great. That was back when they put out mints and cookies (I think) on the pillows and there was music and TV in the rooms! They also gave out paper slippers that say "LakeShore Limited" on them, which I still have in the unopened package. (Might be worth something one day! LOL!) I also recall that the food was spectacular. I was really like a little kid -- overjoyed.
I also remember that when we got to Chicago, I froze my butt off because I had only brought a trenchcoat with me from Ohio -- a silly move on my part. We froze our butts off in Chicago, but it was a lot of fun and very romantic.
I think this trip was also where I realized I was with the man I would one day marry.
But, that is a different story!
-- Jackie