… use the orient point ferry. I’ve taken the Port Jeff ferry a bunch of times, and it’s great, but it drops you right on 91, and 91 is the major route into New England. It’s basically always traffic bound, sometimes badly so, and southbound they have this infuriating merge down to one lane to get onto 95 that is always congested. More generally, the Hartford ->New Haven stretch of 91 is just bad all around. If you’re willing to spend an extra hour or so in travel time in the service of a more relaxing trip, take the orient point ferry. You have to make your way off the north fork to 495 using the ~40mph route 25, which takes about an hour, but you pass through often picturesque wine country and long island coast, with beautiful old victorians, quaint old villages, and not much of the suburban sprawl that characterizes most of long island.
The CT portion of the trip is great too, compared to the 91 corridor – I used route 32, route 2 and route 395 from New London, and they were much less congested than the alternative. You end up deposited on 91 just south of Hartford, meaning you skip all the worst of the congestion because most all of the new england folks have skipped off to 84 and 90.
I’m not sure if I would be as pleased with this route if I was heading to my Mom’s place, since she’s another 45 minutes from where the Lords live (which is where I was recently, for Mike’s surprise 40th b-day bash), and I’m not sure how it will be in the summer when the city folk head out to wine country for the weekend, but I’m going to try it a few more times and see.
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You should try coming down Rt 15 to Rt 8, that drops you off basically at the ferry in Bridgeport. Gets you off of 91 for a good portion of the trip. 15 is a parkway so no trucks though at times it feels a bit tight lane wise, but for your sporty car it should be fine.
Be fore warned, route 25 in the Summer can be _really_ slow on the Island. Though the NewLondon/Orient Point ferry service is better, to get to central LI from 91 south, follow Drew’s advise and use 15 aka the Wilbur Cross/Merrit Parkway with your sporty little car!