Chatham is on the elbow of the Cape, about 50 minutes from 55. The unofficial shark capital of the Cape is an "Old Cape Cod" town with old mansions, narrow streets, and lighthouses; now with boutiques, art galleries, expensive lodging added. Where the Nantucket Sound meets the Atlantic though provides for some beautiful scenery.
Squire - semi-legendary bar/restaurant on the main drag
Chatham Pier Fish Market - doesn't get fresher than this
Chatham Bars Inn
Art installation on Main Street
Lighthouse beach