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The Best of Cape Cod

Tara Donne The Wellfleet Marketplace.

Photo: Tara Donne

The Lay of the Land

Bounded by Buzzards Bay to the west, Cape Cod Bay to the north, and Nantucket Sound to the south, Cape Cod juts out into the Atlantic Ocean like a crooked arm making a fist.


Upper Cape


Perhaps to confound outsiders, the names of the four distinct regions don’t really make geographic sense. The Upper Cape should be called the West Cape (or the Side Cape), since it runs north to south along the Cape Cod Canal and Buzzards Bay. On the “shoulder” of the arm is Sandwich, the Cape’s oldest and most historic town. To the south are the more residential Bourne and Pocasset. In what would be the armpit is Falmouth, though its boutique-lined main street and windswept waterfront facing Vineyard Sound suggest nothing so uninviting. Across a small spit is Woods Hole, a little fishing town and home to a famous oceanographic institute.




The only region with a name that actually makes sense, the Mid-Cape really is the middle of the peninsula. Hyannis, that famous Kennedy enclave, acts as Cape Cod’s big city—and is therefore often avoided by residents from other parts, unless they need to shop at the mall, get their car repaired, or catch a ferry to Nantucket or Martha’s Vineyard. But the place does have a buzzing downtown and the appealing sheltered coves of Hyannisport. (Many towns on the Cape comprise several smaller hamlets, one of them usually designated a “port.”) The Mid-Cape also includes the wealthy, whitewashed village of Osterville, Barnstable Village (the largest town on the Cape), family-friendly Dennis, and Yarmouthport, great for shopping and restaurants.


Lower Cape


Confusingly, this area doesn’t just include the lower reaches; it runs from the elbow of the arm all the way north to the crook, at the bay. The best-known town is Chatham, with its delightful downtown, picturesque lighthouse, and shifting Atlantic Ocean sandbars. The Lower Cape’s other atmospheric villages are Brewster, nicknamed the Sea Captains’ Town (more than 50 of them once lived here); Harwichport, a former whaling center; and Orleans, on a site that allegedly hosted its first European visitor in 1003—Leif Eriksson.


Outer Cape


Another puzzle: the Outer Cape encompasses both the inner, western side of the forearm, bordering Cape Cod Bay, and the protected Atlantic beaches of the Cape Cod National Seashore on the eastern side. The peninsula starts to get narrower and the landscape wilder in Eastham, which has no town center per se, but plenty of walking trails and beaches. Next up is Wellfleet, a longtime magnet for artists and (curiously) psychotherapists. Bracketed by dunes, narrow Truro is lined with waterfront cottage communities. Last stop: Provincetown, also called P-town, a haven for gay men and women, painters and photographers, writers and poets, fishermen and whale-watchers.

Where to Stay

On the Waterfront

The clapboard Chatham Bars Inn, in Chatham, was the first luxury hotel on Cape Cod and is still its toniest address, with prices (and a bit of attitude) to match. The place was opened by a wealthy Boston stockbroker in 1914, and you’ll feel transported to his era when you’re gazing at the ocean from a rattan chair on the wide porch. Across town on a sailboat-filled inlet, the Wequassett Resort & Golf Club, on Pleasant Bay, is Chatham’s other top place to stay. A 1740’s Colonial with lanterns has been converted into the main reception area; most guest rooms are in clapboard cottages scattered throughout 22 acres of gardens. The Little Inn on Pleasant Bay in South Orleans is down the road next to a cranberry bog, and sits high on a hill with fantastic views of the shoreline. White slipcovered furniture and pickled-wood ceilings create a beachy vibe. On a clear day you can see Martha’s Vineyard from the nine-room Inn on the Sound, atop a bluff in Falmouth Heights. The motel-style Crow’s Nest Resort in North Truro isn’t the height of style, but its simple rooms have full kitchens—and you can walk right off the back porch and onto the bayside beach. Once run by the Coast Guard to protect boats navigating the Cape Cod Canal, the Wings Neck Lighthouse, in Pocasset, can now be booked by families or other groups. The keeper’s cottage has views of the water from every room, three sweet bedrooms with vintage-style coverlets, and a gas grill and picnic table out back where you can cook the lunch you caught that morning.

Small Hotels

In the center of Sandwich, the Belfry Inne occupies three restored buildings, including a former church and the Painted Lady, a turreted 1882 Victorian house. Chatham’s Captain’s House Inn feels like a village unto itself; besides its captain’s cottage, there’s a Greek Revival mansion and converted stables. All the rooms at Eastham’s Whalewalk Inn & Spa are furnished with antiques; the most romantic is the tiny Salt Box Cottage. Ask the owners about the best hike and they’ll send you to a place most locals have never heard of. Almost directly across the street from each other, sister properties Crowne Pointe and the Brass Key Guesthouse, in Provincetown, are both compounds of 19th-century houses centered on a pool and gardens. And they both attract a very social (and mostly gay) clientele.

Cottage Life

The Cape is covered with bungalow communities built in the 1930’s through the 1960’s. The houses look adorable on the outside, but the interiors often don’t measure up. An exception: Eastham’s Cottage Grove, whose knotty-pine paneling and vintage furnishings channel a Maine camp. The Colony of Wellfleet was originally an art gallery and hostelry for collectors. Ten Modernist cottages with slightly worn Midcentury furnishings are tended by owner Eleanor Stefani, who feels like your eccentric great-aunt. The more recently built, privately owned Cottages at Mau Shop Village, in the New Seabury resort development, are handled by both owners and rental agents.


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