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Driving New york City to Bar Harbor Me

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I Have never been to the East coast we are planning on driving from St Louis to Hershey Pa then we notice NYC Is only a little further. That being said we are now panning on driving to NYC. Now here are my questions we thought about parking outside and taking a train in to NYC the a friend suggested taking the high speed train to boston, well heck Bar Harbor is just a little further. So now i am not sure what to do. Do we just drive all the way from NYC to Bar harbor or take a train to Boston and rent another car to drive to BH. Then I have read about Whales, Fall colors, light houses, The traffic getting out of NYC going through NH. I just always wanted to eat a LOBSTER fresh off the Boat in Maine. We are going to be in NYC Nov 11. Is Any of this Possible?

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