Seems like you have more than enough opinions on the train versus driving, etc., so nothing to add there (other than saying Mahwah seems like the worse option).
It does seem like a ton of trouble to have come all that way to the most iconic city in the country during the most iconic season and rushing in and out just long enough to see a show. I agree with others – meet the relatives at the show but go earlier and at least take in a few sites, all easily within range of where Hamilton’s theater is. Of course you’ll see Times Square (because its near the theater and you walk by from the train station) but I wouldn’t hang out there longer than the photo op – its actually the worst place in NYC. But the winter market at Bryant Park just a block east would be perfect, and right next to the iconic main library. Or the ice rink and tree at Rockefeller Center, just a few blocks north of that.
Or if you’re looking for something totally different and nice and warm inside, right next to your train station (Grand Central), you could go to The Summit – the 3 story viewing “experience” at the top of one of NYC’s newest skyscrapers, where you are higher than the Empire State Building. I’ve done many famous top of building viewing experiences, and this one was an order-of-magnitude better than the rest. You can see all of NYC, but that’s honestly the least interesting thing about it. The floor is a mirror and the whole thing is surreal.
There’s obviously a thousand other things to do in NYC but I was just listing a few that could be done in a couple hours near where. you will already be.
(side note, if you’re planning a sit down lunch or dinner, the restaurants very near Times Sqaure and the theater district are generally a worse experience than the rest of the city – way too crowded and usually not great food in what is otherwise a city with over 10,000 places to get great food.)
Sounds like a great time, but know that the area around the theater will be very crowded on the Saturday before Christmas. Hopefully, the weather will be decent and you can walk around.
If you are into seeing the iconic NYC Christmas sites, I would suggest going first to Rockefeller Center to see the tree and decor, then up 5th Ave to see St Patricks and some decorated windows. If you are there in the morning, should not be too crowded.
Depending on timing. can then either go up to Central Park, go to the market at Bryant park , or continue to just walk around. We ate at Bond45 right across the street before seeing that show. Definitely touristy but tasty food and easy access to the theater.
If you aren’t into holiday sites and are into art, you could probably zoom through a bit of the Museum of Modern Art before going to the show. A short walk from Grand Central. Other museums would require subway rides.
Subway is not so fun, and there is some expense for 5 people. But… it has advantage of being inside/warm, with more schedule predictably (no traffic delays).
I really appreciate everyone’s advice! It’s given me good information and perspectives.
We live in kind of east central Massachusetts, just a bit east of Worcester, and not near a commuter rail line, so Amtrak the whole way is not as convenient as if we were in a location close to the train.
I live in the Stamford area - I-95 from Stamford to Norwalk is a disaster, even on weekends. Plus the parking garage at Stamford is under construction. I would vote for somewhere further north on the line as your starting point.
There’s a 7:15am semi-express train from New Haven that arrives at GCT 2 hours later (9:15am) on Saturdays. You can use the MTA Train Time app to plan your journey.