Hoping to travel round-trip from Portland, ME (or Boston) to Chicago with my 2-year-old! Willing to do a roomette but also open to making each way a 2-3 day trip and sit in coach to make it cheaper/sightsee along the way. If we were to split up the trip, we have friends/family in the DC area, as well as the NYC area, so we would love to stop in either city at some point. If we're not in a roomette, I think we could realistically do up to 8 hours traveling at a time. Having a really hard time planning different legs of the trip on the website and hoping someone has done a similar trip before! This trip is for May 2026.
r/Amtrak is not associated with Amtrak in any official way. Any problems, concerns, complaints, etc should be directed to Amtrak through one of the official channels.
I am a bot, and this action was performed automatically. Please contact the moderators of this subreddit if you have any questions or concerns.
I did Seattle-> Portland Maine two years ago. Two roommette (empire builder and cardinal), one Acela and one coach. I stopped by Cincinnati, DC, Philly, and Boston for a few days to visit friends
You could potentially do the rail pass and use that to break up your legs
If your looking at taking the cardinal, it runs 3 times a week
However, it shares it's route with the crescent which runs daily until Charlottesville [CVS] only downside is that it'd 2.5 hours aways from DC.
The cardinal is only 24 hours total.
West Virginia is BEYOND beautiful.
If your gonna crash a couple nights. Charleston West Virginia is where I would do it.
This is a wonderful idea, and I have done similar (eastern NH departing, not ME) trips multiple times. The first problem coming from the north is that there is no direct train from Portland to anywhere south of Boston. You need to take the Northeaster from Portland to North Station, then take either the green or orange line to Park Street/Downtown Crossing (same station for all intended purposes), then take the red line to South Station, where you can then get on the train to NYC/DC. This transfer 100% doable, it is just annoying and what Amtrak calls a "self transfer," so you are responsible for getting yourself from North to South Station, and they will not hold the train/refund if you miss it. Taking the subway between the two stations takes about 12-15 minutes, depending on time of day, but I wouldn't schedule any layovers less than 45 minutes (about 30 min walk); anything less is a risk. The subway is safe, clean, and easy to navigate; you are only going 3 stops on one line, 2 on another. You can use tap to pay at all stations, or you can purchase a ticket. At all the stations you will be transferring at, there will be an attendant as well as transit police who can help you navigate/purchase fare.
Alternatively, you can drive directly to South Station (not recommended) or drive to the Concord Coach bus stop (~2 hours, $49 round trip) in Portland (others in southern ME as well). They will drop you off right at South Station, where you can then take the train south. However, taking the Northeaster is cheaper and faster, and gives you the whole train experience, so I would definitely recommend taking the train into Boston.
From South Station, there are many trains to take to NYC/DC, but the simplest (cheapest, most frequent) is the Northeast Regional. Going west and traveling with a toddler, I am not much help, but please let me know if you have any more questions about getting to NYC/DC from Maine.
It saves one transfer to take the T Orange Line from North Station to Back Bay Station and board the NE Corridor train there. But if you are taking Acela first class or have a Guest Rewards lounge credential, definitely get the corridor train at South Station and take advantage of the lounge.
North Station to Back Bay is the transfer Amtrak prefers when taking itineraries to/from beyond Downeaster stations. They will ticket you from back bay.
I've personally never done this, just the green/red because I really care about getting a good seat lol
Best to start your journey in Boston South Station so that you begin the first leg of the journey heading towards Chicago on the Lake Shore Limited 449. From there, you have two choices for heading towards Washington DC, either Floridian 41 (which this route has a tendency to get delayed by a lot due to the unusually long length for an eastern US route going from Chicago all the way down to Miami), or the Cardinal 50 (safer option for avoiding delays, but it operates only certain days of the week due to being a much longer & slower route between Chicago & NYC compared to the shorter/faster Lake Shore Limited). Once you're in DC, you got plenty of choices heading up towards NYC (and eventually back to Boston South Station).
Oh God, as someone currently going Brunswick-Cleveland, get a roomette. My poor husband is dying in coach right now. He’s not a resilient sleeper and this is literally hell for him the poor guy.
NYC is the better choice, as you could take the BOS-NYP leg and pick up the Lake Shore Limited from there to CHI.
POR-BON (Orange Line to BBY) BBY-NYP NYP-CHI
This is so helpful, thank you everyone! It sounds like starting the trip at South Station is my best bet and I’ll play around with routes through NYC/DC based on these comments! I’ll post here again, once I book, with the full route. 😊