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New England June Trip

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At the end of a trip to NYC in early June, my wife and I want to add a few days for a jaunt through some of New England. Tentative plan now is to take Metro North to Greenwich, CT and pick up a car. Drive US 7 up through the western part of Connecticut, all the way up through Massachusetts, possibly spending time at Hancock Shaker Village or, instead, later in the trip at Canterbury Shaker Village in New Hampshire. Any opinions on one vs. the other? Then into Vermont, working our way over to Woodstock. Has anyone been to Billings Farm and Museum? From there, we would cross into New Hampshire and work our way up to and eastward over Kancamagus Highway. Then south, maybe to Canterbury as mentioned previously, down to around Peterborough, and finally back to Greenwich.

Is five days enough time? Should the weather be pretty nice? Will we have any problem finding accommodations? (We tend to overplan, but I'd like to keep this trip loose and flexible and not be tied to hotel/motel reservations.) Any must-sees?

I'd be grateful for any thoughts, suggestions, opinions. Thanks.

Rich from Dallas

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