Chatham

At the bent elbow of the Cape, with water nearly surrounding it, Chatham has all the charm of a quietly posh seaside resort, with plenty of shops but none of the crass commercialism that plagues some other towns on the Cape. And it's charming: the town has gray-shingle houses with tidy awnings and cheerful flower gardens, an attractive Main Street with crafts and antiques stores alongside dapper cafés, and a five-and-dime. It's a traditional town (said to have more registered Republican voters than any other town on Cape Cod), where elegant summer cottages share the view with stately homes rich in Yankee architectural detail. In fact, this tiny town by the sea is where you'll find some of the finest examples of bow-roof houses in the country. Chatham's nowhere near as kitschy as Provincetown, but it's not overly quaint, either—it's casual and fun, in a refined New England way.

Because of its location at the elbow, Chatham is not a town you just pass through—it's a destination in itself. During summer months, the town bursts into bloom as hydrangeas blossom in shades of cobalt blue, indigo, and deep violet. And although it can get crowded in high season—and even on weekends during shoulder seasons—Chatham remains a true New England village.