Northern Exposure: A Road Trip along the North Shore of Massachusetts

For decades, Cape Cod has been the “it” place to vacation on the Massachusetts coast. A more easygoing option: a North Shore road trip, beginning only a half hour from Boston. Thank you to Discover Gloucester and Destination Salem for supporting my discovery work.

Travelers to coastal Massachusetts have traditionally flocked to Cape Cod, a quintessential seaside New England community that has lured political and Hollywood royalty for decades. But with overtourism has come a variety of headaches, not the least of which is standstill traffic along Route 6, the main road on and off the cape.

For a native New Englander like me, the easygoing alternative is the “Other Cape,” Cape Ann, and the North Shore coast that surrounds her. Wide open and rich in stony beauty, the North Shore is composed of more than a dozen personality-packed cities and towns. Here I can get my fill of boulder-strewn beaches and intimate harbors. I can amble through hushed forests and scenic walking trails. I can admire historic architecture, and experience unique cultural offerings. And I can indulge my appetite for spectacular seafood and craft beverages.

North Shore road trip: what to do & see in Gloucester

I chose the 94-room Beauport Hotel as my home base. Overlooking Pavilion Beach, it was built in the style of the waterfront hotels frequented by Gilded Age wealthy who used summer as a verb. The rooftop bar and pool offer some of the best views in Gloucester. This year, the hotel added a luxury spa.

The bruise-purple sky over Commercial Street convinced me to forgo a stroll into the downtown and take the hotel’s complimentary shuttle to the Cape Ann Museum. Its exhibits thoroughly document the working-class maritime history of Gloucester, a city of 28,000 people. Director Oliver Barker said, “We exist solely to safeguard their stories in perpetuity.” 

Among other art, the museum houses an impressive collection by Luminist painters like Winslow Homer, Edward Hopper, and Fitz Henry Lane, who explored the effects of light on the landscape; it’s uniquely spectacular here, thanks to the reflective properties of the granite in Gloucester Harbor.

Last year, the museum expanded its contemporary art and events programming via the Cape Ann Museum Green, about a mile and a quarter away at the intersection of Washington and Poplar Streets. The four-acre campus includes three historic structures that date to the early and mid-1700s. It also has a brand-new, 12,000-square-foot continuous exhibition space—open June through October—that flows from the indoors to the outside. A sculpture garden is also in the works.

As I strolled the property, where several painters were working on translating the landscape onto canvases set on wooden easels, I could see why the museum has hung a giant banner outside the main building featuring a ship riding the waves of a tempest. “Storms rage, but Gloucester endures,” it says, a symbol not only of community solidarity during the pandemic, but of the lasting impression this city leaves on any visitor who comes through on a North Shore road trip.

For lunch, I stopped at Seaport Grille. Tourist trap was my first, dismissive thought about the packed dining room. But the restaurant proved me wrong. As I sampled a tequila-and-lemonade cocktail; a tangy, overstuffed lobster roll; and crispy onion rings with a pronounced hops flavor, my second thought was I could get used to this.  

I made my way over to Rocky Neck Art Colony, one of the country’s oldest continuously operating colonies. Located on a cove-hugging hook of land, offers a peek at modern artists working in media like painting, photography, jewelry, and textiles. It counts 250 member artists in a variety of media, including jewelry, pottery, painting, silk screening, photography, and textiles. Many of them have open studios and shops along the main drag. At the end of the street, I trekked up the stairs to the studio of Stephen LaPierre, a colorful character and prolific oil painter of landscapes, local scenes, Americana, and a “Clowns on Cell Phones” series, a pointed commentary on our perma-plugged-in culture. I browsed paintings, pottery, glass, mixed-media art, and more at Gallery 53, a juried collection of the work of several artists, located in a patinaed, tin-clad building that once housed a paint factory.

Back at the Colony’s headquarters and community center on Wonson Street, I met director Courtney Richardson. We toured the village, starting at the brand-new Cove Gallery. “It was really driven by the artists,” she said of the current exhibit, featuring all female painters, photographers, and mixed-media artists. “That initiative has made the organization what it is.”

Every North Shore road trip needs a greatest-hits tour of the village, and Richardson was ready to oblige with a trek past important spots. The park, which hosts free music and meet-the-artists events on Thursday nights. The iconic building on Clarendon Street that served as a model for Hopper’s Mansard Roof; it’snow privately owned and painted sorbet pink. The property managed by Ocean Alliance, a nonprofit that collects crucial data about whales and marine life, at the tip of Rocky Neck, with views to the west of Ten Pound Island, where Winslow Homer lived as the lighthouse keeper in the summer of 1880. He produced about 50 paintings during his stay.

I retrieved my car and headed across the city to Wingaersheek Beach, at the confluence of the Annisquam River and Ipswich Bay. At low tide, I carefully stepped around snails, salps, and small crabs as I walked into the sea along the exposed sandbar.

Back at the wharf, I boarded the Thomas E. Lannon, a 64-foot schooner built from locally sourced woods. As the sun drifted down the sky, casting ethereal light around the bay, we floated past Hammond Castle, built in the style of a medieval château. We sailed by the mini mansions of Magnolia Point, and curved around Eastern Point Lighthouse, which has guided ships through Gloucester Harbor’s treacherous ledges for centuries.

What to do and see in Ipswich, Essex & Rockport

After a tour of Maritime Gloucester, a fascinating, newly expanded museum that details Gloucester’s rich fishing and shipping history, I headed back outside, where the haze of a lingering storm hung over the city. I peeled the button-down shirt from my sticky skin and tossed it onto the passenger’s seat of my car, grateful I’d had the foresight to dress in layers. As traffic picked up, I continued my North Shore road trip on Route 133 West, which curves gently through residential neighborhoods before connecting onto the Essex Scenic Byway. Here it traverses the small, commercial downtown of Essex. It also passes several lush green marshes punctuated by great egrets, their slim, pale figures like exclamation points among the bright grasses.

Famished and overwarm, I stopped at DownRiver Ice Cream, an unassuming, family-run snack shack in Essex. They craft homemade ice cream from a handful of ingredients, and the quality shows. In the heat of the day, my cone of pistachio began to melt as soon as it was handed to me, and I greedily downed it, the frozen treat cooling the back of my throat.

Four miles off the Essex Scenic Byway in Ipswich lies Castle Hill on the Crane Estate. The historic, 2,100-acre seaside manor features several gardens, a Tudor-style mansion, and a half-mile of tree-flanked lawn that undulates down to Ipswich Bay. You can listen to live music here on Thursday nights, or walk the trails to picturesque Steep Hill Beach and Crane Beach, both protected habitat for the endangered piping plover. 

I was just in time for the tail end of a house tour—and when it comes to Castle Hill, this is the best part. Past the top floor, up a spiral staircase, we were ushered up to the mansion’s cupola. I gasped, looking out at 360-degree views, with the bay on one side and the Great Marsh on the other.

The new Great Marsh Brewing Company is a sleek, glass-paneled beacon of beer in downtown Essex. In the industrial-chic upstairs restaurant, I sat at a marsh-view window and dug into an excellent shrimp po’boy and hand-cut fries.

On Cathedral Avenue in Rockport, the Emerson Inn towers above an Atlantic bluff. Built in the 1850s, the 36-room inn recently underwent a face-lift, emerging as a cozy, Art Nouveau lodging. A stay at the Emerson feels something like a visit to the home of a wealthy, eccentric aunt—elegantly snug, complete with swishy bed linens and freshly baked cookies.   

After pocketing a packet of freshly baked snacks from the common area, I headed up the stairs to my third-floor Seaside King Deluxe. Decorated in a mix of antique and modern furniture, the room was elegant and uncluttered. The windows opened out onto an unforgettable view of the Atlantic. I sat in front of them, eating my takeout meal straight out of the cardboard container and watching herring gulls, buoyed on the breeze, swoop over the rocks.

Like many of Rockport’s quirky cultural attractions, the Windhover Center for the Performing Arts is off the beaten path. This year, Windhover partnered with Gloucester Stage to present live theater. As I settled in for a performance, the last pink of sunset gave way to inky blue-black, and the property glowed with tiny globes strung between the trees. 

Sometime before dawn, lightning scraped open the sky. Rain sheeted down over rolling waves. Trees shuddered. The wind whipped the inn’s flag against its pole. I sat in bed, listening to the eternal rushing and retreating of the surf, a sound I know as well as my own heartbeat.

At 10:00 a.m., Bearskin Neck, Rockport’s downtown, was still waking up. I snacked on a strawberry pastry from Helmut’s Strudel as I wandered the rain-washed streets, their houses painted in shades of weathered grey, butter, apricot, and lilac. I poked my head into shops, said hello to their keepers. Transfixed, I stopped along the water’s edge and watched as a bufflehead dove for snacks near Motif No. 1, a charismatic red fishing shack said to be the most-painted building in the United States, and a sailing instructor towed a curving line of boats and their young captains out into Rockport Harbor.

North Shore road trip: what to do & see in Salem

I took scenic Route 127, along the brambled coast from Rockport to Beverly. I resisted the urge to stop at every scenic lookout along the way, but did heed the call of one of my favorite North Shore road trip destinations: Singing Beach in Manchester-by-the-Sea, a half-mile arc of pinkish sand capped by two tall land masses that project into the water. It might be misnamed—Thoreau described the unique squeaking-sneaker sound the sand makes underfoot as “much like the sound of waxing a table as anything”—but the beach still feels magical, especially at sunrise or sunset.

This treacherous, ledge-stubbled stretch of coast is also the final resting site of several shipwrecks. The best-known are the cutter Albert Gallatin, sunk off the appropriately named Boohoo Ledge in 1892, and the schooner Alice M. Coburn, which ran aground on Great Egg Rock in a winter storm in 1923. Closest to shore is the warship USS Granite State, which perhaps proves the old folk wisdom that renaming a ship—it had three monikers—is back luck. All three are now classified as “exempted sites” by the Massachusetts Board of Underwater Archaeological Resources. You can scuba dive to them, though any major disruptions of the sites are not allowed.

By midmorning, my North Shore road trip had deposited me in Salem. If your knowledge of of the city is limited to its infamous Witch Trials, prepare to be floored. Today’s Salem is modern, walkable, eclectic, and foodie-focused, with a population of 42,000 and zero tolerance for intolerance.

I started at the Peabody Essex Museum (PEM), on one end of the city’s pedestrian mall. The PEM’s permanent collection includes everything from a 2,000-pound model of the Queen Elizabeth carved out of solid mahogany to ornate wooden ships’ figureheads, Asian art collected during Colonial voyages, and the Yin Yu Tang, a late Qing dynasty merchant’s home that was disassembled into more the 2,500 pieces and re-erected on the grounds of the PEM. It also houses a rare, six-foot-plus carved wooden sculpture of the Hawaiian god Ku, and the captain’s desk of the Mary Celeste, a brigantine found mysteriously floating, sans occupants, in the Atlantic Ocean (incidentally, this was also a rechristened ship). And it’s home to detailed exhibits on Salem’s spice trade, which put the city on the national map and gave rise to America’s first millionaires.

Although hardheaded Yankee skepticism runs marrow-deep in me, I stopped at Pentagram, the city’s newest witchcraft shop. In a curtained booth, co-owner Leanne Marrama fanned trios of tarot cards over the marble tabletop. She related them, accurately, to changes in my career and the recent death of my mother.

She drew again and announced, “You have a special connection to the North Shore at this point in your life.” The observation was so on the nose that I squirmed in my seat.

As I stood to leave, Marrama swept the cards off the table and back into a deck. One fluttered to the floor: the Ten of Wands. She shook her head. “You’re busy—too busy. You’re always picking up sticks. You make it work, but you need to slow down.”

I swallowed hard, thanked her, and sped out of the shop. Once on Derby Street, the clouds broke open in a sudden burst of rain. I escaped into the light, airy space of Jolie Tea Company, its wall lined with jars of loose teas backlit with soft purple light. After taking a whiff of some of the shop’s many fine, blended selections, I brooded in the corner, my hands wrapped around a cup of Fig Formosa Oolong, redolent with fruit and bright with vivid blue cornflower petals.

When the storm abated, I met my husband for the trip out to Baker’s Island, four miles off the coast in Salem Sound. Accommodations at the Assistant Keepers House are rustic, but that’s the point. A stay on Baker’s is a singular immersion in nature.

We explored the walking trails, traversing rocky slopes and paths lined with bittersweet and brambles. Herring gulls barked overhead, warning us away from their gray-feathered, uncoordinated fledglings, just seven weeks old and still spending more time on land than in the air. We twisted onto another path, down to the beach where we’d landed, then up again. We climbed to the top of the lighthouse, known as “Pa” Baker—“Ma” was decommissioned and dismantled, with a shove off a cliff, in 1921—and watched herring gulls swoop over the open ocean.

In the fading light, we arranged our dinner on a picnic table. Olives, sesame noodles, and international cheeses from The Cheese Shop of Salem. Carignane-Grenache wine from Pamplemousse. Chocolate-covered butter crunch from Harbor Sweets. We devoured all, to the soundtrack of a clanging buoy bell.

Not long after we went to bed, the storm picked up again, a mighty whirl of wind and water that battered the clapboard siding of the house. Through rivulets of rain on the windowpanes, I could see “Pa” Baker standing guard behind the Keepers House.

In the morning, wet grass was the only evidence of the squall. On the boat back to Salem, we puttered along the edges of the island, taking photos, committing it to memory. I tilted my head back, inhaled the salt air, and allowed the sun to warm my eyelids, feeling comforted, contented, home.

An abbreviated version of this story first appeared in the April issue of Travel + Leisure.

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