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Maine v. Montreal

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We're a family of 5 with 3 teenage boys. We're considering driving from the D.C. area to Maine then possibly the Montreal Jazz Festival in late June/early July. My questions are:

If you've driven the northern East Coast can you suggest an alternative to I-95? Is there a scenic route, with a good stopping place and a great restaurant?

If you've been to Montreal via Maine what's the best way to get there? Again, "off the beaten track" with a stop over.

Does this trip sound like a good idea or a nightmare? : ) Seriously, if you have other suggestions, I'm all ears (eyes, anyway).

Thanks in advance and I apologize if this was redundant; I couldn't find my specific questions in the forum.

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