Driving along the boulder-strewn coast of Gloucester, Massachusetts, gives the impression of endless shoreline. Beach rose, summersweet, and milkweed bloom in tight clusters above towering cliffs, their tops desert hues of clay and sand, their bottoms turned inky by millennia of ocean swells. Scenic beaches, where foamy waves slurp against the shore and seagulls trawl the water’s edge for reckless crabs, appear regularly along coast-hugging Route 127. The air is heavy with salt, slightly tacky on the fingertips and damp against the throat. Massive hotels and the homes of the not necessarily famous but certainly capable of dropping a cool few million jut out over the ocean like patrician jaws, glossy and studiously lived-in.
Based on outer appearances, you might be tempted to lump Gloucester in with other picturesque coastal areas of the Northeast. But this would be a mistake. Beneath Gloucester’s stony beauty, its whooshing waves, its tourist-appropriate veneer—the upscale waterfront restaurants, the harbor cruises, the chic downtown boutiques—lies the pulsing heart of a city that doesn’t just follow the rhythm of a different drummer; it leads the entire band.
From Fish to Festivals: Gloucester History
Rumor has it that when French explorer Samuel de Champlain sailed from Acadia through Cape Ann in 1605, he took one look at the unspoiled shores of Gloucester and exclaimed, “Le beau port!”—“beautiful port” (several venues in the city are named Beauport). The city wasn’t settled until eighteen years later, when the Dorchester Company, an English fishing outfit, deposited crewmen on shore to build processing encampments. When the company disbanded two years later, about a dozen winter-hardy men hightailed it for the more fertile land of what is now Salem.
Settlers gradually returned to Gloucester, and it was incorporated in 1642. Although it’s known as the oldest fishing city in the United States, for a good portion of Gloucester’s history, its main industries were timber and shipbuilding.
The eastern coastal neighborhood now called Magnolia became the playground of politicians from Beacon Hill and the wealthy seeking reprieve from the hot Boston summers. They erected massive homes, hotels, and other shrines to affluence, some of which still stand today. Despite the presence of these moneyed interlopers, Gloucester’s residents did what they’ve always done best: created a place to gather and enjoy.
Gloucester, population 30,000, is a city where people take pains to preserve their blue-collar fishing-industry roots, even if the industry isn’t what it once was. It’s a place that holds a four-day city-wide party every June, St. Peter’s Fiesta, complete with concerts and contests, like the Greasy Pole (it’s just what it sounds like). And it’s a place where the mayor herself, alongside family, cooks upwards of 100 pounds of haddock, shrimp, lobster, pasta, potato salad, and more during the festival and invites anyone—literally anyone—to stop by.
Roseanne LeBlanc grew up in Boston and moved to Gloucester nearly 40 years ago. “From the very beginning, I felt like, Oh, my God, we’re on vacation every single day,” she says. “How could you not love it here? You get up in the morning, there’s a beautiful sunrise and the water—or sometimes mud, but even that’s pretty. You go into the downtown, and there’s always something going on.”
Those goings-on include a variety of festivals, an outdoor concert and movie series, dining and shopping, and, of course, plenty of water-based recreation. Still, Gloucester isn’t bending over backward to develop concepts geared toward tourists. John Orlando, who owns the cozy Harborview Inn—he grew up just eight houses down on Western Avenue—says, “Most everything we have is catered toward the local resident. We figure if we like it, you will, too.”
Natural Resources: Gloucester’s Beaches & Trails
Gloucester’s residents-first approach makes it a gust of fresh, salty air in the world of coastal getaways. To wring every drop of enjoyment out of a trip here, plan to do a combination of walking, driving, and boating or swimming.
Get your bearings by strolling some or all of the self-guided HarborWalk Tour, a free trail of 42 stops that pay homage to nearly 400 years of maritime history, arts, and culture. Then head out to the coast; it’s easy to find your way around by keeping the water on your right.
Visit Eastern Point, the southern tip of the peninsula between the Atlantic Ocean and the eastern portion of Gloucester Harbor. Poet T. S. Eliot summered here for 20 years (“The sea is all about us,” he wrote in “The Dry Salvages”), and painter Winslow Homer lived at the lighthouse for a time. Come sunset, it’s easy to see why. Get a better look by walking or fishing on Dog Bar Breakwater, a quarter-mile stretch of granite blocks built in 1904 to keep ships from running aground and to shelter Gloucester Harbor from storms, which offers panoramic views of the water and shorelines.
For a sampling of Gloucester’s inland treasures, go hiking at Dogtown, an abandoned Colonial settlement whose boulders have been etched with words like Kindness, Courage, Integrity, and Never Try Never Win. Or for a more groomed experience, stop at the 600-acre Ravenswood Park, a Trustees of Reservations property with 10 miles of carriage paths and trails through shrouded hemlock groves and magnolia swamps.
Just a couple of miles away, make a detour at Rafe’s Chasm. Follow the short trail through the woods, which opens into sweeping Atlantic vistas with heart-pattering drops down to the water. Cross the lichen-covered ochre rocks, which look like patinaed copper, and peek into the 200-foot-long, 60-foot-deep gorge carved by millennia of geologic shifts and pummeling waterfalls. Listening to the ocean howl through its base at high tide is a singular experience.
Then it’s time to hit the beaches. Top picks include the half-mile-long Good Harbor Beach, one of the city’s most popular, thanks to its tidy shoreline, stunning views, and rolling, dune- and marsh-covered backside. Good Harbor is what scenic New England beaches are made of, but parking in the summer is a bear—and not cheap, at $35 on the weekends. Go early in the morning or in the late afternoon to maximize your chances of finding a spot.
For a less crowded feel, head to Stage Fort Park and Half Moon Beach, where those founding fisherman first landed. Half Moon is small and sandy, with a tall rocky knoll at the back that casts cooling shadows on sunny days. Take a dip while watching fishing boats, sailboats, and seabirds bob in the harbor.
For an even more secluded experience, try Cressy’s Beach. Its entrance deeper through the woods of the park means Cressy’s doesn’t get the traffic of its better-known sister. This makes it prime real estate for stretching out, relaxing, reading, and picnicking.
On your way out of Stage Fort, stop at The Cupboard, a ’50s-style no-fuss favorite among locals for fried clams, barbecue chicken, cheeseburgers, and other comfort foods. This cash-only diner isn’t the place for health-conscious cuisine, but it’s a must for mammoth servings of hand-scooped ice cream—the kiddie portion comfortably feeds two adults—from nearby Richardson’s Farm.
Exploring Gloucester Harbor
The harbor is big business in Gloucester, and one of its finest experiences. Harbor tours and schooner rides give you the scenic drive-by, while water shuttles, with all-day hop-on/hop-off access for $10, allow you to disembark and explore. But the biggest kaboom for your buck is a whale watch, which offers the zippy, open-air enjoyment of a harbor cruise combined with glimpses of the Stellwagen National Marine Sanctuary’s most extraordinary residents.
For example, 7 Seas Whale Watch—which delivers on the Guaranteed Sightings! their banner proclaims—offers a nearly three-hour tour narrated by a boundlessly enthusiastic naturalist. The boat glides through the dozens of harbor buoys earmarked for different fishermen, the shore of Boston about 24 miles in the distance. It passes Eastern Point Lighthouse and Magnolia Island, made famous in the Henry Wadsworth Longfellow poem “The Wreck of the Hesperus,” and Thacher Island and its twin granite lighthouses, the only fully operational multiple lights in the United States.
From there, you’ll leave land behind for southern Jeffrey’s Ledge, where finbacks, humpbacks, and minkes, their silhouettes glowing green with phytoplankton, surface, exhaling warm air that transforms into that familiar spout of water vapor. No matter how many whale watches you’ve been on, it’s impossible not to race from starboard to port for a glimpse of the massive creatures resting at the top of the water or diving, with a tail-flip flourish, for snacks.
Virgilio’s: A Gloucester Dining Gem
And now a public service announcement for those who love Italian foods but know that the prospects of finding quality homemade breads and pastry outside of major metro areas is fairly dismal: Virgilio’s Bakery, a Gloucester institution since 1961, is a must-stop on your North Shore travel itinerary. Now run by the third generation of the Virgilio family, this blink-and-you’ll-miss-it deli has what you’ve been searching for. The imported oils and pastas are worth noting, but the real story here are the sandwiches, made with imported meats and cheeses, the specialty breads, and the pastry. Especially the pastry.
Choose from cookies like crunchy amaretti, creamy-sweet ricotta pies, and old school buttery pastries such as sfogliatelle. But the real stars are the cannoli, made with a perfectly crispy, not-too-thick shell stuffed with a ricotta-sugar filling that dances right to the edge of sweet without going over the top. Prices are very reasonable and the bakery is closed on Sundays, so pick up a bunch to satisfy your weekend sweet tooth.
Gloucester Downtown: Food, Drink & Shopping
Despite its easily manageable size, Gloucester’s downtown has as much to offer as its coast. For shopping, hit the brick sidewalks of Main Street. Standouts include the Brass Monkey for funky home goods, accessories, and gifts; Pop Gallery and Buoy for clothing and artisanal jewelry; The Cave, a cheese, wine, and chocolate shop; and Pastaio Via Corta, which stocks imported Italian specialties along with its house-made, fresh organic pasta.
While we’re on the topic of food: Gloucester’s dining scene is competitive with the best of the North Shore. You’ll find classic and modern takes on New England fare like fried fish and seafood casseroles, casual cafes with vegetarian and gluten-free options, upscale fusion venues, and several ethnic choices, courtesy of a long history of immigration (Italian and Portuguese restaurants are especially strong. See the sidebar for dining suggestions). Fresh fish is the stock in trade of Gloucester, with bluefin tuna, monkfish, cod, red fish, dogfish, calamari, and lobster gracing menus on the self-guided “bait to plate” seafood tour.
For the swankiest dining experience you can get while clad in shorts and sandals, book a reservation at the Beauport Hotel’s 1606 Restaurant & Bar. It gets busy, so patience is key, but the cocktails and food—heavy on seafood, with Mediterranean and Asian influences—is worth the wait. And you can’t find a better spot than the restaurant’s back deck for watching Gloucester’s spectacular sunsets.
Drift, casual café by day and cocktail and music lounge by night, is a newer entry on the Gloucester dining scene. Kurt Hosman, co-owner with husband Rick, is part of a more recent influx of professionals who’ve responded to the need for amenities that appeal to younger generations. “There’s a lot of talent in Gloucester,” he says. “The visual arts and handcrafts have always been strong, but it’s becoming a very musical area. We wanted to support this, and give people a place to gather.”
The craft beverage scene is also growing. Ryan & Wood Distilleries led the way as the first North Shore distillery since Prohibition. Ryan & Wood crafts small-batch rum, whiskey, vodka, and gin, complete with illustrations of local landmarks on the labels. Co-owners Bob and Kathy Ryan give one of the most informative tours around, providing a behind-the-scenes peek at the distillery and the history of the craft-beverage movement on the North Shore.
The Ryans are career transplants from the fish-processing industry, and are visible symbols of Gloucester’s ongoing evolution. “Gloucester has been going through a big transition,” says Bob. “It doesn’t have to be fish all the time. We can find new industries, do something else. But we’re still loyal to who we are. That’s what Cape Ann is about.”
Custom of the Country: Gloucester Arts, History & Culture
Mayor Stefatia Romeo Theken believes that Gloucester’s working-class history is one of its biggest distinctions. “I don’t have to sell our beaches; they sell themselves,” she says. “We love when you visit them, but we want you to spend a day and learn about our working waterfront and what makes this city what it is.”
Use left and right arrows to enjoy the slideshow below.
To be sure, part of what makes Gloucester tick is its maritime history, represented in several venues. Maritime Gloucester, a good bet for families,hosts a working waterfront, museum, and small aquarium. And the small but well-curated Cape Ann Museum offers exhibits on local history, art, and culture, and an impressive archive, for those who trace their roots back to the area. And there’s the Man at the Wheel statue on Stacy Boulevard, which commemorates the more than 500 residents who have been lost at sea.
Another part of Gloucester’s considerable charms is its independent spirit and love of the arts. A great example is the lesser-trafficked cultural gem Hammond Castle, the estate of inventor John Hays Hammond Jr. (designer of radio remote control, the basis for modern missile guidance systems). Just a few miles from Stage Fort Park and decidedly non-Disneyfied, as American “castles” go, Hammond Castle is a grand, Renaissance-style chateau. Visit the exterior for free, and marvel at the incredible views of the Atlantic, and details like gargoyles, walls fortified with glass shards, and a miniature drawbridge that leads to a pair of imposing solid iron doors with oversized doughnut knockers (see if you can resist quoting “What knockers!” from Young Frankenstein). Or take a guided tour around the extravagant interior and Hammond’s collection of European artifacts.
To sample the work of living artists, drive to Rocky Neck Art Colony, one of the country’s oldest continuously operating art colonies, and once the stomping grounds of plein air painters like Winslow Homer and Edward Hopper, and modernists such as Stuart David, Nell Blaine, and Mark Rothko. It’s now home to dozens of artists working in media from ceramics and textiles to photography and jewelry. Most shops and galleries are open only in summer, but even in the off-season, the streets are worth strolling for the pretty pastel cottages, neat neighborhoods, and waterfront restaurants and bars.
End your visit with another walk along the water. Better yet, find a friendly local who’s willing to take you out on his or her boat. As Hosman puts it, “You go out onto the ocean, and nothing else matters anymore. Everything just becomes peaceful.”