Where the ramble on the East Coast – Berkshires and southern Vermont?

So I’m thinking, with our four free days on the East Coast in early September, we can go so many places in a few hour’s – which I loved when I lived in Boston and later Stamford, Connecticut. (So different from Michigan, where I grew up…and here in Iowa.)

Right now, since we’ll be in NYC and then Connecticut and then end up on Long Island, our best bet may be to go to the Berkshires (North Adams, perhaps) and then to southern Vermont (maybe the famous Dorset Inn in Dorset or a splurge at the Inn at Sawmill Farm in West Dover, which oddly enough was formed in part from my cousin’s vacation home that I visited as a child.) Both are places my husband’s never been to and places I long to return.