Twenty five years ago I did a number of Montreal-NY round tripls by Greyhound and they were quite pleasant. There were these bus-plus affairs that went non-stop in about 7 hours and served a box lunch (ok it was pretty bad, possibly even worse than airline food, if possible). About 15 years, I did the same trip and it was awful, stopping at every rinky-dink town in northern NY State and taking more line 9 hours. Some years ago Greyhound bought out the local bus company and a pleasant 2 hour non-stop between Montreal and Ottawa has deteriorated into a many stop 2 1/2 trip, but the main problem is that the busses are awful with many broken seats.
Now for the last several years my wife and I have taken AMTRAK from Montreal to NY on or near Christmas. First off, it is very cheap, about $200 for two round trips (that includes a 15% senior discount). A trip by air would cost us at least $500 and that would be a good price. To go by air would require getting to the airport 90 minutes early and take us to, say La Guardia, a $30 taxi ride to downtown Manhattan, maybe more. The flight, should it be on time is only slightly over an hour. The train takes usually around 10 or 11 hours (it is scheduled for 9:30, but is always late), but leaves us at Penn station, less than $10 taxi from my daughter’s. Yes, the time is longer, but the lack of hassle almost makes up for it and the price difference does the rest. I have to say that my wife brings a bottle to piss in (and then empties it in the toilet) since she won’t sit on the seat. The johns are not kept clean although they start out in decent condition.
Someone mentioned NY-Philly. I have used that train innumerable times. The Amtrak takes only about a hour and half and you have to have be crazy to fly, since you kill more time than that at the airport. It is fairly expensive, about $90 I think. There is an alternative: NJ transit change at Trenton to Septa. Takes an extra hour, but at a quarter the price. The difference is even more striking for seniors since Septa charges I think $2 (one way) outside of rush hour. You need a PennDOT card but anyone over 65 can get one.
Twice I have taken the RT between Vancouver and Seattle. Leaving aside the feeble-minded customs agent I ran into once (the following dialog is not exaggerated: Where do you live? Montreal. Why were you in Canada? Huh? Why were you in Canada? We lie there. Oh, do you have any prescription drugs? No, I lied since I had overheard him tell someone else that no prescription drugs could be imported), I found it quite pleasant and on-time. The train from Seattle arrives arond 11:30 in the morning, the return is at 6:00 PM and from listening to people talking to the customs agent it is clear that there are a lot of Seattleites that go up spend the afternoon in Vancouver and come back the same day. The RT cost on the order of $50–heavily subsidized by Washington State.
One basic problem with AMTRAK is that they own no track. This means they have to yield to freight trains run by lines that do run the track, their speed is down to whatever is required by the poor maintainance of the owners (the overnight train through Vermont disappeared when a part of the track was condemned and the owner chose not to repair it) and the gov’t would like to end passenger train travel and will not support it, although it is far the most energy efficient way to go. European trains are very good, very fast, mostly on-time, and very expensive. They are also heavily used. Given my choice I would choose to go with a higher fare if they could do the Montreal-NY trip in 7 hours with some reliability.
Funny story: Several years ago taking the NY train in late December, we stopped somewhere along Lake Champlain. The conductor explained that the engine had stalled and they were trying to restart it. After an hour they announced that they given up and the northbound train, which would be along by and by, would push us back to the last station and busses take us to Albany where we would get a regular Albany-NY train. About ten minutes later the train started and we were on our way. I went up and asked the conductor what happened. He said that the controller in Albany had suggested as a desparation measnure that they reboot their computer and try again. They did and the engine started right up. Way to go Microsoft!