Years ago my wife and I went on a train trip that left New York at night and arrived in Montreal in the late AM. Lots of fun. Not too expensive. Unfortunately that’s been off the Amtrak schedule for some time now. But are there any other overnight trips that start in NY? Or Philadelphia? Or New Haven?
Are you looking specifically for an Amtrak sleeper train? 'Cause if your goal is simply to sleep on a train seat, there’s always the LIRR from Penn Station to Montauk for much less of a fare. Or just stay on a subway train all night (the A train is the longest route). Nobody ever gets kicked off at a terminal stop and the ride is just $2.
The Amtrak Cardinal goes from New York to Chicago via Washington and West Virginia (yeah, it’s a little circuitous.) Sleeper cabins are available, and the trip takes 18 hours or so.
The Amtrak Crescent goes from New York to New Orleans via DC and Atlanta. It’s closer to 20 hours, probably. It also has sleepers available.
Or you could try the Lakeshore Limited from NYC to Chicago. If you do go to Chicago, make sure you get one of the long haul direct trains, rather than being routed through DC. If you do that, you’ll only have local coach service from there to Chicago.
Long distance train travel is fun; everyone should do it at least once, when they have the time. Accomodations are the major expense, but you do get all your meals included. And the food is pretty good, too.
For some reason, Amtrak diners and cafe cars only sell wine by the half bottle. You can’t buy just a glass.
As a younger man I took a train from Union Station in D.C. to Miami via Amtrak which was a 23 hour train ride.
SIlver Star and SIlver Meteor run between NY and Miami, and offer sleeper car service.
Lake Shore Limited runs from NY (or Boston) to Chicago.
The Crescent to New Orleans leaves ad midday and runs through the night as it passes through Virginia and the Carolinas. Sunrise and breakfast in Georgia as it takes a westward turn.