The town of Wellfleet (pop. 2,493) is one of the Cape’s most picturesque communities, favored for some reason by writers, psychiatrists, and oysters. Although home to a cluster of fine art galleries, crafts and clothing shops, and pricey restaurants, the place succeeds handsomely in finding a niche between self-conscious quaintness and residential seclusion. It’s also blessed by a Cape Cod rarity: Mayo Beach just west of the town pier, a public beach with year-round free parking.
Wellfleet also has some of the Outer Cape’s more affordable rooms, at the historic Holden Inn ($125 and up; 508/349-3450), 140 Commercial Street, where you share bathrooms, the front porch, and the bay views.