This half-mile stretch cuts a sandy swath into the rocky terrain of Cape Ann's coastline, giving picnickers plenty of sheltered space to spread out and dig in. Nearby, the Kitchen Witch makes packing the basket effortless with gourmet sandwiches, pints of pasta salad, and homemade cookies. Work off your lunch with a romp in the invigorating tide pools, or let your repast settle as you lie back and wallow in the view. Beach Street; the Kitchen Witch, 4C Summer St., Manchester-by-the-Sea, MA 1944, .
The long lines don't lie: Arnold's serves fried clams at their messy best alongside the fluffiest, tastiest onion rings we've ever eaten. The location doesn't hurt either: It's right on the Cape Cod Rail Trail, with picnic tables in the shade of tall pines where you can pitch your kickstand and enjoy surprisingly reasonably priced seafood on a cafeteria-style tray. As a gesture to gourmets, there's even a raw bar. But stick to the specialties: fried clams, steamers, lobster, and corn on the cob. Rte. 6, Eastham, MA arnoldsrestaurant.com/.
This tiny bakery makes breads, sandwiches, and European-style pastries worth searching out—plus unbelievable muffins, pies, and wedding cakes. But what puts it over the top is its inelegant-sounding "dirt bomb," a dense, indulgent breakfast pasty dusted with cinnamon and sugar. It's a sweet way to jump-start any Cape Cod morning. 5 Cottage St., Orleans, MA cottagestreetbakery.com/.
The food at Fin is subtle at first, but soon shows its adventurous side. Take the chowder. It's a go-to order at any restaurant on the Cape, but Fin uses oysters instead of clams and adds a drizzle of white-truffle oil. That level of detail and savory depth permeates the offerings here, from the flawless pan-seared scallops to the salted-peanut ice cream. 800 Main St., Dennis, MA fincapecod.com.
In a neighborhood that's more about hot dogs than haute cuisine, it can be hard to get a decent meal. That's where Audubon Circle comes in. This darkly lit, sleekly cool restaurant with the long slate bar has a small but satisfying menu of dressed-up pub grub, from the downright delicious burger with spicy home fries to the rare seared tuna with garlic mashed potatoes. The legendary pot stickers (dumplings and steamed vegetables served in a paper takeout container) can provoke food fights—over who gets the last bite. And thanks to the expertly mixed drinks and ample supply of local and national beers on tap, there's plenty to please diners and drinkers who long for more than the watered-down suds at Fenway. 838 Beacon St., Boston, MA auduboncircle.us/.
If brunch is the most civilized way to dine, the Harvest is the most civilized place to have brunch. First there's the restaurant's lovely garden patio, which in warm weather offers a leafy retreat from the traffic of Harvard Square. Then there's the table presentation. No paper napkins and messy tabletops here—brunch at the Harvest is a white-linen, Sunday-best affair. But it's the menu that renders this restaurant a class above, with its three-course, prix-fixe ($33) menu of gourmet takes on classic dishes. The eggs Benedict, for instance, are served not one but two ways: crab and avocado on one orb, smoked ham and asparagus with roasted red pepper hollandaise on the other. Omelets come with such citified ingredients as wild mushrooms, spring onion, or pancetta. It's the final course—dessert—that makes this tradition a proper indulgence, from the milk chocolate panna cotta to the irresistible classic chocolate layer cake. 44 Brattle St., Cambridge, MA harvestcambridge.com/.
Want a side of local color with your Devil's Purse pint? Pay a visit to this neighborhood hang, where Cape Cod memorabilia—from family crests to vanity plates—fills every inch of wall and ceiling space. It's not all about the kitsch, though: Bartenders behind the lacquered wooden bar aim to please, and the late-night menu satisfies with grub for both landlubbers (burgers) and seafarers (fish and chips). 38 Main St., Orleans, 508-255-5165; 429 Main St., Harwich Port, 508-430-0404; land-ho.com. 38 Main St., Orleans, MA 2653, land-ho.com.
Cape Cod sometimes feels as though it's sinking under the weight of its many ice cream shops, but Sundae School rises above with handmade, creamy flavors in such addictive permutations as espresso crunch, Kahlúa chip, and Bass River mud (coffee ice cream with fudge, almonds, and chocolate chunks). Add such toppings as fresh, plump blueberries, bananas, buttery hot fudge, homemade cream, and a fresh Bing cherry, and you've got more than just an ice cream treat. You've got a religious experience. 606 Main St. (Rte. 28), Harwichport, MA sundaeschool.com.
Vacationers can play it two ways as they settle into this welcoming, wood-filled space for a midday meal: fuel up for an afternoon of high-impact romping in the sand, or just plain fill up for several hours of indolence under the sun. For the former, there's leaner fare such as grilled chicken on Portuguese muffins and a salad with gorgonzola, walnut, and sun-dried cranberries. For the latter, choose from plus-size portions of clam chowder, crab cakes, fish and chips, and other Cape Cod classics—and enjoy the wistful glances from those sticking to moderation (poor things). 23 West Road, Orleans, MA 2653, beaconroom.com.
For the second year in a row, we've been unable to resist the delectable charms of Radius patissier Paul Connors. The mere mention of his name in Greater Boston sweet-tooth circles produces a range of reactions from barely audible moans to downright drools. Chef Connors' meal-ending treats are passionate, inspired, and sometimes even quirky: The guy is as adept at "candy cape mushroom ice cream sandwiches" as he is at classic creme brulee. And he's a team player: Connors' desserts are the perfect complement to executive chef Michael Schlow's elegant continental dishes, never overshadowing their savory flavors. Calling all pastry chefs: Consider the bar raised. 8 High Street, Boston, MA radiusrestaurant.com.
Every beachside community needs a restaurant with a view, a meeting place of sorts where families and friends can gather for birthday celebrations or just to gaze and graze on a sunny afternoon. For the mid-Cape, that place is the Pelham House. After a recent major refresh, a heated roof deck offers unobstructed Nantucket Sound views all around, not to mention a killer menu featuring plenty of fresh seafood. As for the apré-dinner scene? Multiple fire pits surrounding the sea-level dining area are perfect for cocktails and moonlit ocean views. 14 Sea St., Dennis Port, MA 02639, pelhamhouseresort.com.
Based solely on the coolness of its bayside pool, Wequassett would swim away with this prize. But it also excels in every other way: The cozy cottage accommodations feel like the Cape of yore (albeit with Molton Brown toiletries and nightly turndown service); prime Signature rooms have fireplaces and unmatched water views. And then there's the exquisite golf course. The outdoor bar. The laid-back yet attentive staff. Need we go on? 2171 Head of the Bay Rd., Harwich, MA 2645, wequassett.com.
Surprise—not everyone on Cape Cod covets pressed khakis and leather loafers. Step out of conservative Falmouth and into Maxwell & Co. to find cutting-edge American and European looks by Strenesse, Etro, and Twilltwentytwo. Teens and grandmothers alike are sure to find something appropriate in this large space, which also carries clothes by Lacoste, Ted Baker, and Robert Graham. 200 Main St., Falmouth, MA shop.maxwellandco.com/.
The Cape has its share of pubs ready to get you good and sloshed, but if you'd rather savor a drink than slam it back, the Nor' East Beer Garden, in Provincetown, is an excellent choice. The tiny, shirelike oasis has an extensive list of craft beers, and its selection of inventive, garden-infused cocktails (consider an arugula mojito or a "rhubarbarita") offer some peaceful refreshment amid the antics of Commercial Street. 206 Commercial St., Provincetown, MA noreastbeergarden.com.
Seven thousand yards of championship golfing, nestled in 170 acres of sweet-smelling pine forest: The 72-par Dennis Pines is a course to be reckoned with. With water at four of the holes, enough trees to test anyone's accuracy, and the notorious par-5 twelfth, the course is arguably the toughest—and certainly one of the most beautiful—on Cape Cod. Amenities are plentiful, including an expansive driving range and practice green, a nice little lounge, and a well-stocked pro shop. Rte. 134, East Dennis, MA dennisgolf.com/.