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Having lived in Boston, other than Boston itself, there's not much of interest to see in eastern MA. (Rte 6 on Cape Cod is pretty, but you'll trundle along at 35-45 mph the whole time.) However, the western portion (the Berkshires) of MA is beautiful. Lots of great roads there, as well as in western CT such as around Lime Rock. Most of the pretty towns of New England, IMO, are north of Massachusetts (such as in VT and NH). You can take Hwy 100 up north through VT to towns like Stowe and Killington area. That's a very pretty drive.
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1987 Venetian Blue (looks like grey) 930 Coupe
1990 Black 964 C2 Targa
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