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Fall Foliage in New England

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My wife and I are coming to the US in late September (about the 28th but flexible) to see fall foliage in the New England region. Our plan is to fly into Boston, recover from the flight from Australia for a couple of nights and then head to either Bar Harbor or Portland for three nights, then across to Hamilton for three night and then to either Stowe or Bennington for three nights.
From there we will head to West Point, Harrisburg, Monticello finishing up in Maryland visiting friends.

Do we have a reasonable plan to catch fall colour?
Any recommendations on towns to stay in?
Any things we should see along the way

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