@m99255j: I have taken the Amtrak train several places, even had a sleeper car once. I almost always enjoy train travel, if I have a good book, companion, and no crying babies or loud singing people on my car (it happens!).
Amtrak is funny about how you reserve things, and the reservation website is weird with navigation. They do have a phone-in system and a travel newsletter or travel planner. I last used this 2010-2013, so my data may be old.
There are rail passes that you can buy that allow multi-city, multi-on/off privileges. Requires some research!! There are black out dates, and sometimes to get where you are going, you might have to layover longer than you want in city for which you had no interest, to make the travle plan work.
Sometimes you arrive in bad parts of town at 2AM, and might wait overnight or 3 hours for the next train!! Sometimes, your main leg of travel might not start until 11:18PM. So there are weird hours.
I usually traveled with a companion. Tried to travel solo a couple of times, but the aforementioned details sent me packing back to the airport!
Having said all that, I have traveled from Richmond, VA to NYC multiple times on Amtrak, without event, other than normal delays and other travel frustrations (2 hour layovers in DC, etc.). That I have done solo several times...it's a daily run so felt safer? Same is true of legs from VA to DC and has mostly to do wtih the fact that the hubs you arrive and depart from have lots of people, food, cabbies, and train leaving/arriving every 5-30 minutes.
I have also traveled North to Niagra Falls from Jersey, which required a couple of cab rides and 1 car rental, plus foot travel pulling luggage over the bridge from the US to Canada. 
I think I also traveled near Chicago. That took 3 days, and I had a sleeper car. (that was for a medical emergent second opinion issue, so that trip wasn't really for fun).
I have also done a few of the silver bullet or aecela express or whatever the name is for the train that goes from Davis CA to Reno NV, through the Rockies.
I loved eating in the dining car. I have also traveled VA to Orlando FL or somewhere near that. I think you have to be under 30 to enjoy sleeping overnight in a train chair! (Now if I have to travel overnight on the train, I allow for a sleeper car, or I fly. Sadly, mostly I fly now)
Train travel is definitely doable and enjoyable! READ ALL THE FINE PRINT. Make sure you have looked on the map where the train depots are, coordinating what time you will be arriving or departing from the depot, and how you will get to your final hotel or whatever destination. IE, At 2AM will cabbies be standing by? Will the depot lobby be open for longer than the 10-minute de-training? Research, Research!
Good luck! Let us know how it goes?