I've driven this route about six times in the last two years, and honestly, it's pretty good. The trip takes about 4-5 hours, depending on when you leave and how many coffee stops you make. The stretch through Connecticut can be picturesque, especially during the autumn foliage season. During rush hour and on Friday evenings, traffic can be very heavy, so it's important to time your trip right. Parking in Boston is definitely challenging, but the compact city centre allows you to get around on foot. Overall, a road trip from NYC to Boston can be quite rewarding if planned correctly. Here are more details on this topic
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