It's a fairly short ride, ~5 hours between the two and there's not much in CT. Maybe Foxwoods or Mohegan Sun casinos.
I would probably take the coastal route and stop around Newport RI.
Take the coastal route, I-95. Stop in either Old Saybrook or Essex CT. It's a lovely part of the state and there are many wonderful B&B's and Inns in that area with 5-star restaurants, etc.
You could also choose to stay at Foxwoods or Mohegan as mentioned, if you want to visit a casino. My personal preference is for Mohegan Sun.
Here are some links to the B&B's, etc. I've stayed at the Copper Beech and it's amazing. Definitely book a dinner at their restaurant if you stay there...or even if you don't.
If you want the most scenic I would suggest taking US 7 north thru Connecticut and Massachusetts passing thru Kent, CT and Stockbridge, MA and then turning right in Williamstown (another lovely town) on MA Route 2 (the Mohawk Trail) and proceed to Boston. Williamstown would be a spot to consider staying overnight.
It depends on what you want to see.Edited: 10 April 2013, 18:26
Others have suggested the coastal route. You could take I-95. Nothing much to see on the Interstate, but there are things to see in Connecticut. There is Mystic with the Seaport and Aquarium, and a nice downtown. The seaport village of Stonington is lovely. It is a short trip from there to Newport as mentioned previously.
Good suggestions from Howland_Owl. I especially like the first suggestion.
Another very different option would be to drive out to end of the North Fork of Long Island (through wine country and pretty coastal scenes), take the Orient Point Ferry to New London, CT. It's right next to Mystic. You could chose to overnight on Long Island before taking the ferry.
I'm a big New Haven fan: Yale, and its free art museums (Yale Art Gallery, British Museum of Art). There is also the Peabody Museum of Natural History. Toads music club for nightlife. My favorite pizza place; Pepes Pizza, and another local instiution; Louis' Lunch...birthplace of the hamburger, so they say.
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