Founded in 1969 and recognizable by its wrought iron roadside statue, Titcomb’s Bookshop has evolved from a small antiquarian book dealer into a three-story business with an international following. Stop in to flip through A History of Chowder, grab a game for the kids, or pick up a paperback to bring to Sandy Neck Beach Park just up the road. Lifeguarded from Memorial Day to Labor Day, the beach is accessible with a parking sticker or a day pass ($15-20). Go for a dip, read under your umbrella, or take a short hike on the nature trail to look for signs of deer, reptiles, and wading birds. After a little sun, continue into Barnstable for a visit to Cape Cod Beer, a craft brewery that proudly advertises “a vacation in every pint.” Cape Cod Red, a full-flavored amber ale is their bestseller, but on a hot day, Beach Blonde, a golden-hued easy drinker might be a better choice. Time your stop with a tour and tasting (Monday-Saturday), or grab a growler to go (from $11).
A bit further in Yarmouth is the Edward Gorey House, a small museum dedicated to the author, illustrator, and playwright best known for his darkly comic book The Gashlycrumb Tinies. Four rooms of exhibits include puppets, prints, a raccoon coat, as well as all sorts of curiosities that Gorey collected during his lifetime. Tucked away in a marina beyond the town center of Dennis, the Sesuit Harbor Café runs cruises aboard the 58-foot Lobster Roll, but you don’t need your sea legs to enjoy enormous sandwiches or views of the Bay. Grab a picnic table outside and sit down with a roll full of succulent lobster meat in a mayonnaise dressing with diced celery and a slice of fresh tomato. An equally large scallop roll ($10.95) with a lemony tartar sauce is similarly tempting. If you’re still hungry or need a dose of caffeine, pull over at the Hot Chocolate Sparrow in Orleans, just across from the popular Cape Cod Rail Trail. This coffee and chocolate bar does a brisk business in lattes, cappuccinos, and hand-dipped candy, but they also sell something called a Magic Bar ($2.95), a gooey, chewy square of walnut, caramel, coconut flakes, marshmallows, and chocolate chips on a graham cracker crust. It’s big enough to share.
On the other side of the Cape’s elbow, Chatham has preserved much of its historic character and is considered the quintessential Cape Cod town by many. Park near Main Street and walk southeast toward the ocean and Chatham’s lighthouse station, established during the presidency of Thomas Jefferson (free tours most Wednesdays through the fall). Window shop at boutiques along the way, browse at one of the art galleries clustered at the intersection of Chatham Bars Avenue, or silence a grumbling stomach with some local fare at The Impudent Oyster. This restaurant’s small size, dim lighting, and stained glass windows lend it a romantic quality, adding to the appeal of a place where every night seems like Saturday night during high season. Service is friendly, the seafood is always fresh, and portions are large—the baked Lobster Mac & Cheese topped with panko breadcrumbs and Parmesan ($14) could easily be a main course, especially if you start with the raw bar and plan to save room for a piece of warm blueberry pie for dessert.
When it comes to seafood though, Wellfleet, just past Cape Cod National Seashore and First Encounter Beach, where the Pilgrims came in contact with a group of Nauset Indians, reigns supreme. At the top of Main Street The Wicked Oyster poses an upscale option for diners who prefer their entrees on a white tablecloth. Order the pan roasted catch of the day served with littlenecks, leeks, bacon, and fingerling potatoes and wash it down with a glass of local Chardonnay from Truro ($10), or one of seven martinis on their cocktail menu. For a more casual option, follow Commercial Street to Wellfleet’s town pier and choose between three more eateries: Mac’s Seafood, Pearl, or Bookstore & Restaurant, where oyster stew with sherry offers a twist on the more ubiquitous clam chowder. Get your meal with a different view on the other side of the peninsula at The Beachcomber, a favorite due to its setting on a bluff overlooking the Atlantic.
And then, finally, there’s lively Provincetown, a hybrid of maritime history and contemporary culture. Sure, a climb to the top of the 252-foot-tall Pilgrim Monument provides fantastic views all the way to Boston on a clear day, but the real action is down on Commercial Street, or on Race Point and Herring Cove Beaches at sunset. There, the sky’s bright pastel colors might inspire you to take an art class. Which isn’t to say the town itself lacks color. In the distance of less than a mile you’ll find funky galleries, fishing boats, gay bars, quirky theaters, and striking examples of Greek and Gothic Revival architecture. For a cool treat as you stroll along the main drag, order one of the “adult flavors” like White Russian or Mudslide Chip from Lewis Brothers Homemade Ice Cream at the corner of Standish Street ($3.75 for a single scoop). And before heading out on a sunset stroll, a dune tour, or maybe a movie back at the Wellfleet Drive-in Theater, consider dropping by a cheery pub and oyster bar called the Squealing Pig, where those who’ve already had their fill of shellfish can get a Hog Burger with thick cut bacon, gorgonzola, spicy chipotle onion and a pile of crispy of Tuscan fries.