The 60-something mile stretch where route 1A hugs northern Massachusetts, clips New Hampshire and meanders into Maine is a magical trail of craggy seascapes, dotted with manses that beg to inspire opulent ghost stories. This trifecta of seaside towns—Rockport, MA, Portsmouth, NH and Kittery, ME—make for a sweet 6-7 hour sojourn from New York, filled with quaint inns, great eats and vibrant artist colonies well worth exploring over a long weekend.