Update!Need advice regarding 1st Amtrak trip in 37 years ...

I always carry on - I just put the weekender above my seat and my tote under my legs after I adjust footrest.

I never use the dining cart, I just bring a couple of snacks and bottled water. However, my trip is only about 10-12 hours.

There are outlets.

I haven't done your trip, but we took the train from DC to NYC over spring break. I don't recall an option to check my luggage, but the porter may have done that. There were racks on each end of each train car and you could put your luggage there. There were also racks over our heads.

I didn't use the dining car, but DH did to get coffee. The kids also went, but came back with just chips. Yes, it was expensive. But I know they loaded more food on in Baltimore. We left DC at about 7:30 am and arrived in NYC about 12:30 pm, so we just got lunch at Grand Central. I did have snacks on the train and we ate breakfast before we left.

There was an outlet for each set on the wall of the car. So the person in the aisle seat ideally could have a longer cord to make the reach. There was wifi on the train, but it wasn't that fast. I wouldn't try streaming anything. It did shut off while they changed engine cars in Baltimore.

On the way back from NYC, it was a beautiful day--warmer than forecasted. But evidently the thermostat is set at a central location. The porter said that they had to shut the system down to change the settings. Several of us requested this to be done and she did it happily. I think she was warm too, but a passenger has to request the change. It took about 10 minutes and the fans were up and running again with cool air. So I'd suggest dressing in layers.

They did check tickets. We got on at a small stop south of DC. He checked our tickets and put a slip of colored paper above our seats. The tickets were checked again in DC and then again after Baltimore. The porter was changed out in Baltimore, too. Same thing on the way back.

It was a pretty slow trip and sort of bumpy. But we were on the regular train, as the express train was another $150 per ticket, IIRC. It was still easier than driving and gave DH a nice break (he does most of the driving.) It had been a busy spring and I wanted a nice, easy going trip before DS goes off to school in the fall.

Never been on a train trip, so I have no advice. It's something I'd love to do someday. Have fun!

I've taken the train twice, both trips were about 5ish hours. One to Toronto I don't think had a dining car, we just brought our own snacks and a pop. The train to Chicago had a dining car but we brought sub sandwiches with us. I believe we bought a pop and chips tho. Please don't take KFC like one other passenger did, it smelled up the whole car. Plus she kept sucking her teeth the whole rest of the way. That was about 20 years ago and we still laugh about her, with sound effects.

what a cool trip to take your boys on! mine would have loved something like that this will definitely create some great memories for all of you.

I take the train fairly often from NYC to central NY state. Every train I've been on in the last few years has had one outlet per seat. However, I've been in cars where the outlets on one whole side of the train did not work, so be prepared. If your train has wifi, it may be slow and it may be intermittent. If you will be using sound on your devices, be sure you have headphones/earphones.

The seats have tray tables that fold down, and a reading light.

You can check on Amtrak.com to see whether your train has wifi, a cafe car and/or a dining car.

As stated above, don't be surprised if your train is late departing and/or arriving at your destination.

Yes, you can take your cooler tote. If it's big enough, I'd fill a ziploc with ice; it will help keep your food cold and you can use the ice for drinks if you take cups. You can also get ice from the cafe car. I think the cafe car cannot heat food that you carry on. On one trip, the girl that sat with me brought a salad and a bottle of wine to drink. Be thoughtful; this is not the time for super smelly food! Also, there are several tables in the cafe car. You may be able to use a table in the cafe car if the three of you want to eat together, but sometimes people camp out at the tables (instead of using their seats) for the majority of the trip.

On the trains I've been on, every car has 2 bathrooms. If the bathrooms on your car are nasty (they can be, especially at the end of a longer line), use the bathrooms in another car. I'd also take a roll of TP (In case the bathroom runs out), some tissues, napkins and antibacterial gel.

If there are no seats for you and your son, ask the conductor if there is anything they can do. I've seen them ask people to move in such situations. I've also volunteered to move when I've seen parties of 2.

Enjoy your trip!

DS and I took the train to Portland a few years back, from Los Angeles.

We had a roomette, which included all meals in the dining car. The food was great, for transportation food. We carried bags on for the outbound trip, not knowing we could check. We checked on the return, but ended up waiting two hours for them when we got back. HUGE bummer.

Our roomette had outlets, but no wifi. Things might have changed in the interim, but it was a bummer at the time. We usually could get some connection when we were in the stations.

I would not take an overnight trip without a roomette or suite. It added to the expense considerably, but it was an awesome part of the venture.

So glad you enjoyed it and it was a positive experience. I hesitate to recommend trips on AMTRAK, because people often don't have the best experience - or are expecting something way different (luxury of the Orient Express maybe? LOL )

The California Zephyr has some amazing scenery through Colorado.