A lot will depend on the time you are leaving and plan on getting to Fairfield County and around NYC. I'm Metrowest Boston and do the OBX trip several times a year. There are several routes, and some are preferred depending on the time you are going. GWB can be iffy. Fine at night.
84 - 684 - Sawmill to Tappan Zee. Then GSP to 95.
84 - Charter Oak Bridge - 91 - Wilbur Cross/Merritt - 287 to Tappan Zee.
Merritt Parkway can be bad for traffic. Only two lanes. 84 in Danbury has had a lot of traffic the past few years, too.
I grew up in Fairfield County. 95 in Fairfield County was to be avoided in the past. Traffic on the Merritt had been so bad lately that GWB/95 is actually back in play again for me after avoiding it for decades.
A lot of traffic has even driven me to even use the Newburgh Bridge on 84 to cross the Hudson.
If you have a lot of time and want to do something scenic, there's another way across the Hudson that doesn't see much use. Bear Mountain Bridge. I was making good time and thought it was bumper-to-bumper to the Tappan Zee coming home, so I decided to do that. Pretty neat. Was the world's longest suspension bridge for a little while. A bit out of the way to get to from both NY and CT sides, though. Scenic overlook over the Hudson on the east side of the Hudson. I pulled in there to try to figure out where the hell I was.
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