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8 day day road trip Sept-Oct from Long Island to CT,MA,NH

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Hi
Does anyone have any great ideas for a road trip this Sept - Oct , some towns to go through.
We are planning a trip from Long Island to Connecticut, Massachusetts, and New Hampshire.
We have about 8 days. I would like to make a loop. Thinking about taking the ferry to CT head up to NH (doesn't have to be near coast) then loop around to come back on the west side of NH, MA, CT. We would Love to stop at some Apple orchards and fall festivals, lakes, and to see some starry nights. We have a 14 month old so some light nature walks is important to us. So far I read about the Golden rod taffy machine haha, and Gould Hill heirloom apples.

Thank you

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