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Train. Don't drive. It's a very long ride (roughly 2 hours), although if you can get the new "super express" that stops only in Bridgeport and Stamford before Grand Central, it's not that bad ("only" about an hour and forty). Still, it's an exhausting commute if you do it more than a few times a week. I used to go twice a week and that was fine; I'm currently at 4 times a week and it's pretty rough. If you love NYC (as I do) it makes it better. I would not do it 5 times a week and would prefer to do it only 3 times.

This is a wonderful rundown.

MNRR is nearly always on time, and the electrics they run are the most reliable trains in the country. The trips are padded, so you may get into Harlem or GCT early, and always early into New Haven. It's only 4-5 mins from West Haven.

But it's way too expensive. Interstate CT fares are okay. Try transit or biking to the station to save on a permit & stress. Have a good lock, though, on both frame and at least front wheel. There are covered spots outside next to the garage.

If you're within an hour, daily commuting to NYC would be fine.

If you live farther out than that but still on the rail line, then 2-3 times a week is probably OK, especially if you can take an express train. More than that would get stressful.

If you're in Hartford or somewhere like Guilford or New London, then maybe once per week would be OK.

In the above, I'm assuming that once you get to NYC, you do not have another long train ride. Commuting from CT to NYC is pleasant if your office is at or very near Grand Central than it is if your office is somewhere down in Lower Manhattan. You can get a lot of reading done on Metro North, but waiting for and riding subways in addition to that adds a lot of stress

I used to walk across brooklyn bridge to work 45 mins just to avoid a 3 stop subway ride. I had to remind myself of all the reasons why I left ny in the first place. I declined the job offer even though they negotiated with me down to 2 days office work. Thanks for the insight.

I did from Milford. Agree any more than 3 days a week is really rough. Especially now that hybrid and remote work is so much more prevalent.

Makes sense. The worst part about a combined subway-train commute is the unpredictability of the subway, especially if you are doing an additional transfer. Because that means you don't know if you'll make the train you want to take home, unless you leave a lot of extra "just in case" time. At least with walking or biking, you pretty much know exactly when you'll arrive.

If we all lived in Central and Northern Europe where the trains run like clockwork every 5 minutes it would be different.