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More for romance, tree lined streets, beautiful homes, cute little stores, great dining. I am thinking Martha's Vineyard. Having trouble choosing a B&B. Is it easy to get to Nantucket from Martha's?
What you're describing sounds more like Maine than Massachusetts, although Boston has superb dining. It sound like you want a laid back trip to quiet old country, which you'll find a lot more easily in Maine.
October is NOT the time to go to Woodstock. It is a lovely town but during foliage season is PACKED with cars and shoppers. Crowded and NOT intimate. Better other times of the year.
It is easy to get from Martha's Vineyard to Nantucket. Ferry runs from Oak Bluffs and takes 2 hours. Probably stops Columbus day, though. From your description the Vineyard and Nantucket will fit well