That's late enough to avoid most traffic, except the I-95 Cross Bronx which is always busy.
Why would you be taking I-95 vs. 84 or the Merritt? Personally, if there is anyway I can avoid I-95, I do, unless its wicked early in the AM or late in the PM. Between New Haven, Bridgeport, and Stamford, there is just too many possible traffic issues. Even if traffic isn't stopped or slow, it is usually heavy and full of trucks, even around 6:30-7 when you'd be driving it (although you would be going "against the grain" of traffic.) The Merritt simply parallels 95 and is usually a much more pleasant drive (and just as easy to get to I-287 as 95).
From Boston it would be also just as easy to take 84, and besides Waterbury, there isn't nearly the city congestion of I-95. And I-684 is a breeze down to 287 or the Hutch, whichever way you go.
I would still recommend the Merritt or 84/684 to Hutch/Cross County/HH/GWB parkway route I mentioned above. I don't use GPS but I imagine specific routes can be programmed to make it easy to follow? But if you are wary of the multiple roads, I would recommend the TZ/287 via Merrit/Hutch or 84/684 as opposed to I-95 to TZ/287 or worse to the Cross Bronx and GWB.