The town of Wellfleet (pop. 2,750) 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, clam shacks, and pricey restaurants, the place succeeds handsomely in finding a niche between self-conscious quaintness and residential seclusion. It’s also blessed by Mac’s Seafood (508/349-0404), just west of the town pier, which sells fresh fish, shellfish, and ice cream cones, best eaten just before a glorious sunset over the bay.
If you’ve never watched a movie in the comfort of your own car, it’s time you caught up with lost pleasures at the Wellfleet Drive-In and Cinemas (508/349-7176, $11, cash only), on US-6 four miles north of Eastham. The drive-in is a genuine throwback to the late 1950s era of roller-skating carhops and T-bird convertibles. There’s also a four-screen indoor cinema, open year-round.
Wellfleet also has some of the Outer Cape’s more affordable rooms, at the historic Holden Inn (140 Commercial St., 508/349-3450, $115 and up), where you share baths, the front porch, and yet more bay views.