The four towns on the Lower Cape are primarily family-oriented summer communities. In the quaint village of Harwich Port, the beach is a mere block off Main Street, making it easy to indulge in the eternal summer pleasure of strolling barefoot with an ice cream cone. To get to Chatham at the Cape's elbow requires an intentional detour, which may have helped preserve that town as a charming and more upscale locale than some of the other towns along the Nantucket Sound. With its Main Street lined with appealing shops and places to eat, Chatham approaches an all-American, small-town ideal -- complemented nicely by a scenic lighthouse and plentiful beaches nearby.
Occupying the easternmost portion of historic Route 6A, Brewster still enjoys much the same cachet that it boasted as a high roller in the maritime trade. Save for a relatively recent incursion of condos and cars, it looks much as it might have in the late 19th century; its general store still serves as a social center. For some reason -- perhaps because excellence breeds competition -- Brewster has spawned several fine restaurants and become something of a magnet for gourmands.
As the gateway to the Outer Cape, where all roads merge, Orleans offers more variety in the way of shops and entertainment than some of its neighbors. Its nearby cousin, East Orleans, is in itself a destination, with a couple of fun restaurants and -- best of all -- a chunk of magnificent, unspoiled Cape Cod National Seashore.