My father used to say that you were guaranteed good weather if you spotted a boat as you drove across the Cape Cod Canal—the thin strip of water that separates the 70-mile-long peninsula from mainland Massachusetts. As our Ford Pinto station wagon rattled over the Sagamore Bridge, my brother and I would press our foreheads to the window and hope for a sighting. To this day, I religiously scan the water every time I hit the bridge. It’s my signal to myself that I have left the real world behind—and it’s just as reassuring as that first whiff of briny air or the sight of pine needles mixed with sand along the roadside.
When I was growing up, my family rented shingled cottages in Chatham or Dennis, or stayed with friends in a beachfront apartment in Provincetown or a Victorian house in Harwich. A vacation on Cape Cod was all about simple pleasures: fishing off the Chatham drawbridge with my grandfather, putt-putt golfing in Dennisport, watching movies at the Wellfleet Drive-In Theatre (I saw Jaws there and, like half the country, was terrified to go in the water for years afterward). On sunny mornings, we’d debate whether to make the trek to the wide, wild beaches of the National Seashore or head to one of the placid coves on nearby Nantucket Sound. Gray days meant decamping to Provincetown, where my brother and I would create spin-art masterpieces at a toy shop while our parents explored the galleries. No trip to the Cape was complete without a platter of fried clams from a roadside shack.
Later I discovered the Hamptons, with its designer shops and sleek nightclubs. The Cape began to feel a bit “ye olde” by comparison; the fudge shops and five-and-dimes didn’t have quite the same allure. But something funny happened in my absence: the Cape stayed the same. When I started coming back after years away, I fell in love with its unpretentious charms all over again. Granted, there’s now a Marc Jacobs store in Provincetown, but my childhood shell shop remains tucked away behind the saltwater taffy store. And despite the influx of big money in Chatham, the town band still plays in the park on summer Friday nights and local fire trucks still lumber down Main Street in the annual Fourth of July parade.
Life hasn’t changed much thanks in part to the locals: Cape Codders are a fiercely protective bunch—a reputation confirmed for me firsthand while I was eating day-boat scallops recently at Abba, a restaurant in Orleans. I made the mistake of telling some fellow diners that I was writing a story on the area. Suddenly they were all over me for my credentials. Did I have a place here? (Luckily, my parents bought a house in East Harwich a few years ago.) What was my favorite beach? Lobster roll? Hiking trail? It was quite an interrogation, but I passed. I guess I had earned my stripes—and the right to lead others to my favorite spots.
Of course, narrowing down the whole Cape, with its myriad charming villages and hundreds of beaches, gave me butterflies. I know some people will ask why I left out a certain swimming hole or a particular seafood shack. But in my humble opinion, these are the places that best define Cape Cod and the joys of summer.
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.
Mid-Cape
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.
Where to Eat
Haute Cape Cuisine
Abba, in Orleans, is widely touted as the Cape’s best restaurant. Israeli-born chef Erez Pinhas dips into his heritage for dishes like falafel in a tahini-amba sauce, then spins the globe to Asia; his shrimp-and-lobster pad thai has a cultlike following. The small restaurant fills up fast, so if you can’t get a reservation, ask for a seat at the tiled bar. Red Pheasant Inn, in a 200-year-old ship’s chandlery in Dennis, sources ingredients from local producers including Not Enough Acres Farm down the road. It’s worth the wait for a table at Terra Luna in North Truro, where Raina Stefani serves up creative concoctions like ancho-and-coffee–rubbed New York strip steak or roasted free-range chicken with bread pudding. With 18 tables in a Cape Cod cottage, the Nauset Beach Club Restaurant in East Orleans is a tough reservation to score. Don’t miss the northern Italian trattoria’s risotto of the day—green peas and fontina cheese one night, wild boar with funghi the next. Set in the basement of a Victorian house, Provincetown’s Front Street is owned by Donna Aliperti and Kathleen Cotter, who can usually be seen in the kitchen making dishes like pan-seared salmon with Swiss chard dumplings, white bean coulis, and sage. For sushi as fresh as it gets, Inaho, in Yarmouthport, has the requisite shoji screens and a Japanese garden out back. Another great sushi spot is Mac’s Shack in Wellfleet, which also serves dishes like coconut-curried scallops and tuna-mango “martinis.” When you’re in a pearly mood: Chatham’s Impudent Oyster, Wellfleet’s Wicked Oyster, and Hyannis’s Naked Oyster are three of the best seafood sources on the Cape. Try to get a table overlooking the sandy beach at the Ocean House Restaurant, in Dennisport, and go deep into the land of fusion. (Roasted black cod with edamame ravioli and miso-truffle broth, anyone?) Consider a jacket and tie for an evening at Twenty-Eight Atlantic, in Chatham’s Wequassett Resort, where dishes range from black-truffle risotto to Chatham day-boat scallops with peekytoe crab, mâche, and a lemon-tarragon emulsion.
Seafood Shacks
At the best joints, the menu doesn’t vary much—fried, fried, and more fried—plus lobster rolls and coleslaw. Cap’t Cass Rock Harbor Seafood is a funky BYOB in Orleans with wood floors, shelves lined with old seashells, handwritten menus taped to the walls, and colorful buoys covering the exterior. Get there on time because the hours are strict (11 a.m. to 2 p.m. for lunch; 5 p.m. to 8 p.m. for dinner). Before you head to the beach, pick up lobster rolls to go from Nickerson’s Fish & Lobsters in Chatham. An insider’s secret, Sesuit Harbor Café is hidden in a Dennis marina, with picnic tables by the water. Order the fried lobster tail at Arnold’s Lobster & Clam Bar, in Eastham—a hit since it opened in 1976. Its new competition is Catch of the Day, in a nearby fish market in South Wellfleet. Liam’s at Nauset Beach, set right between the sand and the parking lot, has legendary onion rings. A couple of other addresses to keep in mind: Sir Cricket’s Fish & Chips, in Orleans, and Provincetown’s Townsend Lobster & Seafood, whose owner, Chris Townsend, runs lobster-catching tours on his fishing boat.
Breakfast
Bonatt’s Bakery & Restaurant, in Harwichport, is nothing to look at—but its sugarcoated Meltaway rolls are dreamy. Another famously decadent breakfast treat: the buttery, cinnamony, muffin-shaped Dirt Bomb donuts at Cottage Street Bakery in Orleans. (Faithful followers have sleuthed out the recipe and make them back at home.) An all-you-can-eat buffet reels them in to Laura & Tony’s Kitchen, in Eastham, in an airy 1970’s-style A-frame across from the Wellfleet Drive-In Theatre (still showing movies all summer).
(Not Just) Lunch
The Dunbar Tea Shop in Sandwich is perfect for afternoon tea, complete with scones and clotted cream. Antique pots line the walls of the yellow 1800’s carriage house. In a tiny cottage with trompe l’oeil rugs painted on the floor, the Brewster Fish House is always packed at dinner; locals know to come during the day. Although it has zero atmosphere, Harwichport’s Talk of the Town Café, wedged between a CVS and a hardware store in a strip mall, sells the best cup of chowder on Cape Cod. The neon-lit exterior of the Lobster Pot, in Provincetown, makes it an often-photographed spot. Order the lobster as God intended it—steamed, with drawn butter on the side.
Picnic Supplies
When the basket demands foie gras or artisanal cheeses, check out the Brown Jug, a gourmet grocery in Sandwich. They’ll also put together a basket for you, complete with cloth napkins and a corkscrew. For simpler fare, try the Osterville Cheese & Sandwich Shop, with a white-and-yellow awning out front and a wide selection of cheeses and wraps. Peter O’Donovan relocated from Ireland to open Chatham’s Nantucket Wild Gourmet & Smokehouse, where he cures heavenly organic salmon on-site.
Afternoon Delights
Practically every town has an old-school ice cream shop with picnic tables outside.
There are vintage black-and-white photos on the walls and birdhouses hanging in the trees at Schoolhouse Ice Cream & Yogurt, in Harwichport, where the intoxicating rum-raisin and Irish-whiskey flavors are for adults only. Sundae School Ice Cream serves unusual varieties like ginger and has three locations across the Cape: the original in Dennisport, plus outposts in Harwichport and East Orleans. In a former blacksmith’s shop in Centerville, Four Seas Ice Cream is the place for Kennedy sightings.
Where to Shop
The Tastemakers
The Cape has its fair share of gift shops peddling potpourri, T-shirts, and other useless bric-a-brac. But a handful of women are transforming the shopping scene. Former set designer Mari Porcari has curated the most fashionable boutique on the Cape: Weekend, in Orleans, in an 1835 general store with birch display tables and lime-green walls. The eclectic merchandise includes summer dresses by New York designer Tibi, eco-friendly bamboo bowls, and floral-printed organic quilts. Missy Smith and Sarah Rhinesmith Buckley, the owners of Chatham’s Midsummer Nights, have a great sense of style. One of the front rooms in their ship captain’s house is devoted to sea-inspired clothes from Tory Burch, Trina Turk, and Calypso. Scattered throughout the shop are porcelain sea urchins, steel lanterns, and other gifts that will create the look of the Cape back home. Sisters Ann Hill and Margaret Hill combined their backgrounds in design and fashion to create Yarmouthport’s Design Works, which sources from abroad (Scandinavian furniture, Turkish earrings) and close to home (totes made in Maine from old sails).
For The Home
To find shabby-chic cottage décor, check out Joan Peters of Osterville. The owner’s signature Cape Cod toile design appears on fabrics, tiles, and even sinks. The go-to place for brightly colored plates, napkins, glassware, and rugs is Periwinkle, in a two-story house in downtown Wellfleet. Always wondered where your grandmother got that rag rug in her kitchen? Check out Harwichport’s Cape Cod Braided Rug Company. Like many resort towns, the Cape has tons of pottery shops. At the pondside Scargo Pottery & Art Gallery in Dennis, you can visit even when the shop isn’t open to wander through a peaceful sculpture garden. The Cape doesn’t lack for antiques shops, either. One of the most comprehensive is the sprawling Sandwich Antiques Center, whether you want furniture painted by Peter Hunt or vintage firearms. In the center of Sandwich, the Weather Store carries barometers, thermometers, and everything else weather-related, both old and new. Run by actor Tony Curtis’s ex-wife, Leslie Curtis Antiques & Design, in Dennis, specializes in wicker.
And Don’t Miss
The Brewster Store was converted from a church into a general store in 1866 and still has the requisite porch, coal stove, penny-candy display, and ice cream parlor. You can buy just about anything here—donuts, puzzles, pitchers, and even lighting supplies. In an open-air stand on the side of the highway, Wellfleet’s Briar Lane Jams & Jellies is your stop for beach plum jelly, rosehip jam, and cranberry marmalade. A beaded mermaid curtain sets the tone at the kitschy Shell Shop, in Provincetown, opened in 1978 to supply beach houses up and down the Cape with shell-encrusted mirrors and starfish for propping in windows. A symphony of chirping welcomes you to the Bird Watcher’s General Store, in Orleans. The staff has tons of personality—if you tell them a joke, they’ll give you a free pencil.
Outdoor Life
Best Beaches
The protected Cape Cod National Seashore stretches 40 miles, from Chatham all the way north to Provincetown. It was set aside in 1961 by John F. Kennedy. Top strands include North Beach (on a sandbar in Chatham and reachable only by boat) and Provincetown’s Race Point (where you can sometimes see whales offshore). Also within the park, in East Orleans, Nauset Beach is beloved for Liam’s (see Seafood Shacks). The six-mile-long, dune-capped Sandy Neck Beach, in West Barnstable and Sandwich, is populated by more piping plovers than people. In North Falmouth, the crescent-shaped Old Silver Beach has calm waters that attract families. Craigville Beach, the place to see and be seen in Hyannis, is sometimes called Muscle Beach for its concentration of buff beachgoers.
Biking
Built on an old railway bed, the 26-mile Cape Cod Rail Trail starts at Route 134 in Dennis and winds through Chatham, continuing north to Wellfleet. There are cyclist-friendly cafés along the way.
For Nature Lovers
One of the hidden gems of Cape Cod is Falmouth’s Spohr Gardens, laid out in the 1950’s by Margaret and Charles D. Spohr and now owned by a charitable trust. An ideal place for quiet contemplation, the six acres of daffodils, rhododendrons, and daylilies edge placid Oyster Pond. Spread across three islands near Chatham, the Monomoy National Wildlife Refuge is a protected area for migratory birds and a popular place to walk. If you’re planning to beachcomb, check the tide charts so that you don’t get stuck; at high tide in some sections, the sand disappears.
Top Tours
The Massachusetts Audubon Society’s Wellfleet Bay Wildlife Sanctuary runs birding tours, seal-watching expeditions, and canoe trips throughout its 1,200 acres of pine forest and salt marshes. Art’s Dune Tours, in Provincetown, take travelers off road through the lunar landscape of the dunes outside town; in the distance you can see the shacks that have been inhabited over the years by Tennessee Williams, Jackson Pollock, and other legends, and are still rented to artists.
On The Water
The bright-yellow vessel operated by Beachcomber Boat Tours offers seal-watching tours or drop-offs of passengers at North Beach (and pickups later). For guided kayak trips with naturalists or sport fishing charters, turn to Goose Hummock, the area’s aquatic experts.
Best Seats For The Sunset
Rock Harbor in Orleans has planted trees in the surf to mark the channel for boats, and they make for a striking silhouette against the colorful sky. Onlookers at Provincetown’s Race Point Beach erupt in applause the moment the sun disappears. To watch with a glass of wine in hand, head to the Chart Room Restaurant, a simple seafood haunt in a marina in Cataumet, where crowds gather on the lawn to toast the spectacle. Add dinner to the experience: at the Red Inn in P-town, the view of the sun setting over the bay is so spectacular that you almost don’t even notice how good the food is. (But try the pan-roasted cod with a lemon-garlic confit, served on a bed of rosemary potatoes and applewood bacon.)
