Scenic Summer Drive in Cape Ann, Massachusetts

This 40-mile journey begins on Route 127 in Beverly, the bustling gateway to Cape Ann, where suburban density gradually gives way to winding roads and saltbox colonials. This is the “Other Cape,” a peninsula of fishing ports, villages, farms, beaches, Gilded Age estates, and fried clams. The geography of this coast—part granite ledges, part sandy shores—evokes Midcoast Maine more than Cape Cod, and we’d argue that the beaches are more dramatically beautiful here than on the bigger cape. That’s one of many reasons to take a summer drive here; another is this year’s 400th anniversary celebration of Gloucester’s founding, with tours, concerts, and festivals throughout the summer.

From Beverly, the road skims the scenic shoreline before heading inland toward Beverly Farms, the neighborhood that gave Beverly Hills its name (Burton Green, an investor, chose it to honor his hometown). A few miles down the road, Manchester-by-the-Sea boasts a picture-book town center that’s worth exploring on foot and the sandy crescent of Singing Beach, which allows visitors to park (for a fee) on summer weekdays.

Between Manchester-by-the-Sea and Gloucester, the Coolidge Reservation is a Trustees-managed property overlooking the Atlantic, and just after that, a right fork off the state highway will bring you through the charming hamlet of Magnolia, which is well worth the detour—as is the stately Hammond Castle Museum, a bit farther up the coast. Then you’ll find yourself in downtown Gloucester, where the working waterfront bumps up against a luxe hotel, historic art colonies still leave their mark, and summer people and locals share in the natural beauty. Here, town beaches are open to the public, with passes available for purchase online (book early).

Following the shore will take you around Gloucester’s beautiful Eastern Point and past Good Harbor Beach, then through idyllic Rockport—a town shaped by the sea, by the granite quarries that helped build New York and San Francisco, and by the artists who have long called it home. Heading back to the highway, you can loop north to boulder-dotted Wingaersheek Beach and linger to watch the sun set into the waters of Ipswich Bay. But don’t miss the chance to visit the old shipbuilding town of Essex on its namesake river, where you can dine on fried clams where they were (by all accounts) invented, shop for antiques and artisan goods, kayak through the marshlands, and learn the history of the schooners that powered New England’s fishing industry.

Yankee‘s Favorite Places to Stop Along the Way

Frank, Beverly: Fuel up with a breakfast sandwich and coffee at star chef Frank McClelland’s combination market, café, and full-service restaurant, which takes its inspiration from local fisheries and farms (including McClelland’s own Apple Street Farm in Essex).

Singing Beach,Manchester-by-the-Sea: Named for the unique squeaking sound that the sand makes as you stroll along the waterline, Singing Beach lets you soak up the sun while gazing out at the whimsically named offshore boulders and micro-islands (Little Salt, Rock Dundy, Boohoo Ledge). There’s a bathhouse and snack stand; for beach reads, Manchester by the Book is just a short walk away.

Coolidge Reservation, Manchester-by-the-Sea: The Coolidge family purchased this land in 1873 and put a grand “summer cottage” on a wide lawn overlooking the ocean. The house is long gone, but the lawn remains as one of the most beautiful picnic spots in New England. Walk up Bungalow Hill for even more expansive views.

Hammond Castle Museum, Gloucester: Modeled on medieval European architecture, this 1920s castle was built for inventor and art collector John Hays Hammond Jr., whose display of medieval and Renaissance artifacts inspired John D. Rockefeller Jr. to build the famed Cloisters in Upper Manhattan.

Cape Ann Museum, Gloucester: Learn about the Cape’s long maritime and artistic heritage at this museum, which holds the largest collection of Fitz Henry Lane’s art (fans will enjoy the neighborhood walking tour that traces his early life and inspirations). A new Edward Hopper summer exhibit is also worth a visit.

Sushi Sang Lee, Gloucester: Chef-owner Sang Hyun Lee’s omakase dinners near the waterfront are intimate, multisensory delights, as Chef Lee walks guests through each course, presented on locally made pottery. This is sushi as an art and a craft.

Talise, Gloucester: Perched over Lobster Cove in the village of Annisquam, Talise takes its cues from local produce and seafood. Chef-owner Joshua Smith’s lobster tacos are made with artisan masa flour; sourdough is freshly baked. Seafood is king here, but there’s also a phenomenal burger. Book early.

Brothers Brew Coffee Shop, Rockport: Homemade doughnuts; cinnamon rolls; a linguica, egg, and cheese breakfast sandwich on an English muffin … these are the makings of a dream breakfast.

Diamonds & Rust, Essex: Allow plenty of time for browsing this highly curated collection of vintage and modern decor and clothing (we love the collection of indigo “chore coats”). Hours are generally Wednesday through Saturday, but call ahead to confirm.

Woodman’s of Essex, Essex: The original home of the fried clam is always worth a visit, thanks to the quality of the (always gluten-free) fried seafood, as well as the homemade chowder, which is not too thick, not too thin, and chock-full of clams.