The Oregon Trail


The town of Wellfleet (pop. 2,79) 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, $12, 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, $50 and up), where you share baths, the front porch, and yet more bay views.


One of the finest biking or scenic driving routes on Cape Cod is the stretch of Old County Road that winds between Wellfleet and Truro (pop. 1,999), on the bay side of US-6. Topography is varied, with hills and dunes, and traffic is minimal, so you can get a full sense of what the Cape is like beyond parking hassles and bijou restaurants. Like Wellfleet, Truro is well off the beaten track and has little commercial development. From the 1940s through the 1960s, Truro attracted a significant summer artists’ colony whose members included painter Edward Hopper. These days, Truro is perhaps best known for the Head of the Meadow beach, just north of the landmark Highland Lighthouse on the Atlantic side of the Cape.

The Truro area also has one of Cape Cod’s most appealing low-cost lodging options: the HI-Truro Hostel (508/349-3889, late June-Aug. only), beautifully situated between cranberry bogs and ocean beach in a former Coast Guard station on North Pamet Road.

Map of the Oregon Trail Route in Massachusetts

Map of the Oregon Trail through Massachusetts.
Map of the Oregon Trail through Massachusetts.

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