North back towards Boston with stops in Ct on the way

Sorry but "stops in Ct. on the way" isn't helpful for giving you advice. WHERE in Ct.? I 95 is just a dreadful road for traffic. If you can avoid it, I would. So I'm saying instead of looking to park as close to Manhattan as possible, I'd look to park to avoid I 95 where possible.

Many times we have driven to New Haven, parked the car in their gated, lit, secure parking garage, and taken the Metro North train, (or Amtrak) into Manhattan for a few nights stay. There are secure parking garages closer to NYC, but not further away from NYC (on the line that goes through Springfield, anyway).

We have also spent a night in a hotel in New Haven, parking the car in their secure gated lot, and then took the free hotel shuttle to the train station for overnight stays. (Several offer this service).

Both are relatively inexpensive options (and Metro North is lots cheaper than Amtrak). If you are coming from MA it is crazy to go all the way around Manhattan into NJ; also if you don't want to drive in the city and pay huge parking fees, then don't. I would agree that it is better to put the car into a gated lot or garage than otherwise.