2007: I took Amtrak on a round trip from the Seattle area to Beaumont, Texas and back [1]. Part of that involves taking the Sunset Limited between Los Angeles and Beaumont. That's a scheduled [2] 40 hour trip from Los Angeles to Beaumont, and 36 hours from Beaumont to Los Angeles.
There was no wifi on the train then (or now, I believe), and I did not have a phone with cellular internet.
The Legend of Zelda: Phantom Hourglass for the Nintendo DS came out in North America just 3 weeks before my trip started, so I saved that for the train trip. I also brought Mario Kart and some other Mario game that I had not finished. Oh, and Brain Age was very helpful--it includes a bunch of Sudoku puzzles. I also had a bunch of podcasts and some audiobooks on my iPod.
I did not bring, if I recall correctly, any physical books on the train. I wanted to travel light, and the books I was currently reading or wanting to read were all heavy hardbacks. (Kindle was not out yet...it was released while I was I was in Texas, a few days before the trip home started).
All I brought on the train was my PowerBook, the entertainment stuff listed above, my phone, a TomTom GPS, a couple charges to keep the aforementioned stuff running, toothbrush and toothpaste, a comb, a swiss army knife, and enough clothes to cover the time on the train.
Everything else I'd need or want for the 3+ weeks I'd actually be in Texas, including several hardback books, I shipped via UPS or FedEx ahead to the hotel.
I don't understand why more people don't do that, at least for stays where they are bringing a lot of stuff. You've already got enough to deal with on boarding day...why add wrangling two or three big pieces of checked luggage to that? And FedEx and UPS lose luggage at a lower rate than airlines (I could not find data on Amtrak lost luggage rates). [3]
[1] for the usual reason one would go to Beaumont, Texas if one has no relatives there. A patent I was involved in ended up owned by someone who sued someone else, and I had to go be a witness.
[2] Most of the route is over track owner by freight rail companies, and their trains have priority. That means AmTrak spends a lot of time sitting on passing sidings waiting for a freight train to pass. Add several hours to scheduled times for any long trip.
[3] I suppose it might depend on how things are getting paid for. Since I was going in order to be a witness in civil litigation, someone else was paying for my travel expenses, and they had a pretty loose wallet. If you are paying for your own trip and your fare includes a certain amount of luggage it might be hard to justify letting that freebie go to waste and paying for FedEx.