Long Island to Ct by Ferry
I don't know where you are starting from on Long Island, but now might be a great time of year to travel along the North Fork and take the ferry from Orient Point to New London, CT. A lot of harvest festivals, farms (pumpkins, corns mazes, apple picking, etc.), and wine country to drive through and make some stops on the way to Orient if you wanted to. You could hit some coastal areas on your way up to Boston, such as Plymouth which is definitely scenic. We just did a weekend trip there in September and really enjoyed it. We stayed based there and took the train into Boston from there one day and spent time in Quincy Market. In our experience, actually driving and parking in Boston isn't ideal.