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Help Me Plan Road Trip from PA to Maine

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I apoligize for posting this again as a new topic but I tried a cut and past this afternoon and made a mess :-(

So once again -- spirobulldog and dfrostnh - Thanks for your comments. We have changed our not very well thought out plans and have eliminated Niagara and will save that for another trip. We can begin May 20 by flying into Phila for a 1 day family commitment.Then pick up a car from there. Maybe we could start out from there and fly back to Florida approx June 5 from Maine.We would like to visit, not necessarily in this order,

1 Bar Harbor and Acadia
2 Portland, Maine
3 Montpelier, VT
4 A nice Berkshire area town with a music and /or performance festival. I know Tanglewood performances do not begin until end of June.
5 Fairfield, Ct (we would visit friends for a day)
6 Newport RI
7 Probably have to drive through some of NY or NJ but would appreciate a suggestion as to where to stop.

We like food and wine, not necessarily upscale and don't want to do winery tours. We were thinking more in the line of lobster rolls and ice cream. We don't really hike but enjoy a healthy walk &/or a bike ride.We enjoy music and art, fairs and festivals,local history, small town shops and stopping to talk to people. We are not on a tight budget and like really nice hotels and B & B's.

Thanks again for any suggestions!
k2

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