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Road trip in New England - What to see?

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I'm so happy about all the tips I got for my US-vacation last year, so I'm gonna try again for our fall vacay!

We are planning on visiting several cities, and after looking around online I'm very interested in driving around New England. I have a friend in Boston, so I'm probably going there either way, and I'm also visiting NYC. In all we have 3,5 weeks to spend in USA, and we also want to visit Chicago and New Orleans. But how long depends on how much time we spend in New England.

I'm thinking that driving through Connecticut, via RI (read about the vineyards:) up to Boston would be a nice trip. Vermont and Maine would probably be too far, but what about New Hampsire, is it worth a visit?
I havent made any itinerary yet, so now I'm just looking for your best New England spots.

We are a couple in our early 30's and we arrive September 13th. I heard that fall is a great time to visit NE.

So any tips you have, for places to visit, places to stay, to eat ++ would be gratly appreciated.

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