My partner and I travel to NYC a lot for work and fun. ORH to JFK is super fast and inexpensive, and can be done round trip in one day. IMO the downside pain is getting from JFK to Manhattan, if that's where you're headed -- though I live <10 min from ORH which compensates.

Love Amtrak because you land in midtown, hate driving to the Rt. 128 station from Worcester. It's (usually) more expensive and takes longer than flying, but I can work on the train.

Another post also says driving is fine -- I totally agree, depending where you're going and timing. Traffic's reasonable except like the last 45 min into the city.