Ahh, makes more sense with the additional context. Working with those parameters in mind... Kent Falls/New Milford (CT), and Great Barrington/Stockbridge/Lenox (MA) are both potentially interesting road trips through quaint pockets of lower NE just around the 4-hour mark. I have also heard good things about Lititz (PA), Annapolis (MD), and Milford (PA)...but haven't visited those three yet.