Your Ultimate Guide to Cape Cod

Picture a quaint village green flanked by a boutique-lined main street and a white-steepled 19th-century church. Welcome to Falmouth. Here, preppy-cool locals scavenge the racks at stylish outlets like Cape Chic, Vagabond Treasures and Twigs, and kids gather at the cute Eight Cousins bookshop. After a stroll through town, pop into Anejo Mexican Bistro for the signature guacamole, made tableside, and tequila (if you dare). Or nosh on classic French dishes — duck confit rillette, lobster strudel, pan roasted Atlantic swordfish — at The Glass Onion. Just make sure to save room for a cone of homemade ice cream (the buttered lobster flavor is damn good) at Ben and Bill’s Chocolate Emporium, where the line often spills out onto the street.

At the farthest fingertip of Cape Cod, P-Town is the most bohemian spot in the state, with a thriving gay scene and plenty of charm. Colorful Commercial Street serves as the main thoroughfare, where rainbow flags are strung between storefronts and visitors swarm the sidewalks. Go on a pub crawl from Harbor Lounge’s private pier (oceanfront martini, anyone?) to Aqua Bar’s raw oyster counter to The Underground’s game room/dance floor. Or go off the map and explore the 40-mile National Seashore, which is dotted with small lighthouses, wild cranberry bogs and our favorite plot of sand, Race Point Beach. Those with the seafaring spirit can spot humpback whales, basking sharks and bluefin tuna on a three-hour tour with Dolphin Fleet Whale Watch.

Trade Cape kitsch for a secluded rural getaway in Brewster. Pitch pine and scrub oak trees border the roads, and a mom-and-pop general store greets beachgoers as they putter in for the season. When the tide rolls out, tour the flats and Brewster Oysters' farm, then head to Brewster Fish House and try some for yourself. Make your base the elegant Ocean Edge Resort, and rent one of its cruiser bikes to pedal the 22-mile Cape Cod Rail Trail; then reward yourself with a frozen mocha at the Hot Chocolate Sparrow in Orleans, a 30-minute ride away. For dinner The Bramble Inn & Restaurant serves a mouthwatering harbor stew, with littleneck clams, mussels, shrimp, scallops and the catch of the day simmered in white wine, or go for French fare at the 300-year-old Chillingsworth estate (a favorite of culinary legend Julia Child’s). End the night with a bonfire and s’mores under the stars on Bay Pines Beach, the resort’s private stretch of sand.

Do you dream of Nancy Meyers-designed beach houses and Nicholas Sparks settings? Well, we can’t promise a steamy summer affair, but this tiny windswept town — the oldest on the Cape — is perfectly preserved in all its 17th-century glory. Former captains’ homes along Route 6A are now quiet B&Bs and antiques shops. Dig through objets d’art at Paul Madden Antiques, consignment finds at Sandwich Antiques Center and rustic beach-chic decor at Treasures of Cape Cod before heading to the Sandwich Glass Museum to watch glassblowing demonstrations and gaze at rows of vivid teal, neon-yellow and lime-green vases.

If Cape Cod is old-fashioned, Wellfleet is its artsy, party-hearty offspring. There’s the Actors Theater, lovely craft studios (LunaSea Studios, Wellfleet Crafts) and art galleries like Left Bank. A young, in-the-know crowd flocks to The Beachcomber for ales and cocktails, live bands and an epic raw bar, all housed in a gray shingled shack that overlooks the bay. Another popular hangout is a flea market by day, a drive-in movie theater by night; it attracts locals along with A-list musicians (Harry Connick Jr. once parked here for a flick with his brood). Grab crispy pains au chocolat and smoked salmon, cream cheese and lettuce clubs to go at PB Boulangerie Bistro for a picnic, or try shellfish and Bloody Marys at the annual Wellfleet OysterFest (October 15–16).

A bucolic enclave in the elbow of Cape Cod, Chatham transports visitors back to the age of maritime men, palatial estates and wild barrier islands cloaked in morning fog. Fleeting sandbars and circular coves surround the town, which is, surprisingly, known for its upscale shopping. Flex that plastic on a medieval atlas at Maps of Antiquity, nautical jewelry at East Wind Silver Co., cookware at Sea Salt & Pepper and high-end children's clothes at Minnows & Guppies.

This postage stamp hamlet sticks to its fishing village roots, serving as the state’s leader in oceanic research. Bring the kids to the country’s oldest aquarium, or learn about under-the-sea adventures at the Oceanographic Institution. The smell of fresh-from-the-oven popovers (and other homemade pastries) at Pie in the Sky draws both locals and tourists bound for the Vineyard. Just over the drawbridge, on Woods Hole’s main drag, there’s a smattering of gift shops and galleries including Local Colors, Under the Sun and Woods Hole Handworks. You’ll find plenty of families rollerblading and cycling along the Shining Sea Bikeway, but we recommend taking a detour to Nobska Lighthouse, which hovers on a bluff above Buzzards Bay and Vineyard Sound. Come evening, Quicks Hole Tavern & Taqueria cooks up quahog chowder and lobster tacos with a side of live jazz.