Gloucester is undoubtedly a destination for tourists. Visitors come to relax on the gorgeous beaches and have a beer at the Crow’s Nest, the bar made famous by The Perfect Storm. They come for an animal-spotting adventure aboard a whale-watching cruise or to delight in the scenic charms of the lighthouses on Eastern Point and in Annisquam.
What makes Gloucester such a compelling place, however, goes well beyond its most obvious attractions, say locals who love the place. It is, they say, a city with deep roots and a strong personality, where creativity flourishes, tradition is treasured, and hard work is central to the community’s identity.
Take a seat at any bar in town, and you’ll be rubbing elbows with fishermen and multimillionaires alike, many whose families have lived in the city for generations, says Kory Curcuru, a Gloucester native and founder of Bridge Cape Ann, an online community and promotional business.
“Status doesn’t really matter here,” he says. “Gloucester’s still got some sandpaper to it. The people are real.”
Gloucester was first settled by Europeans in 1623. The first colonists quickly abandoned the village, but new Englishmen tried their luck again some 20 years later. This time it stuck. And Gloucester has been enduring ever since. That sense of determination and history give the city a distinctive character that distinguishes it from vacation-focused seaside towns.
“It’s important to me that Gloucester has that relationship to work, and not just leisure — that it isn’t just a holiday town,” says Sarah Swift, owner of MAGMA, a movement and dance studio near the city center.
The best way for visitors to get a taste of this spirit is to start downtown. Running along the edge of the harbor, Rogers Street and Harbor Loop combine glimpses of fishing boats sailing to and from the working waterfront with appealing restaurants (try the smoked meat options at Oak to Ember or sip a cocktail on the deck at the Beauport Hotel). Want to do the cooking yourself? Grab some freshly caught local seafood from the mobile fish market.
Running parallel, just a short distance farther from the water is Main Street, where historic brick buildings are home to a host of small, local businesses. Try an Italian pastry from Virgilio’s bakery, browse for new books at the Bookstore of Gloucester or used volumes at Dogtown Books, or find your new favorite outfit at Design of Mine.
“A lot of the businesses here are generational,” Curcuru says. “For the most part, we didn’t succumb to the big-box, brand-name thing. That adds to the rustic New England charm.”
Those seeking the real Gloucester will also need to dive into the city’s arts scene. The area’s stunning natural beauty, picturesque buildings, and a particular light that artists say is very special have long attracted and inspired painters, sculptors, writers, and other creative types.
Winslow Homer painted boats sailing in the harbor, and T.S. Eliot cited his youthful summers at the family home in East Gloucester as an influence on his poetry. And artists—from painters and potters to musicians and dancers—are still creating today.
“There are these long-standing institutions that make a place where artists feel like they can create,” Swift says.
Visitors today can check out the galleries and studios downtown and on Rocky Neck, a quirky, colorful neighborhood that holds the title of the country’s oldest working art colony. The main campus of the Cape Ann Museum, a rich repository of art and artifacts from Gloucester and surrounding towns, is currently closed for renovations, but programming continues at the Cape Ann Museum Green, an annex campus right near the highway. The museum also offers walking tours that highlight the scenes that inspired notable artists such as Edward Hopper and Fitz Henry Lane.
“All of [the tours] represent what is so special about Gloucester and Cape Ann -– the history, the industry, the art,” says Ed Becker, a tour guide for the museum. “It’s fun to get people out there to share that with them.”
For further exploration, head outside the city core. Visit Hammond Castle to learn about an eccentric inventor who built a Medieval-style castle on the Gloucester waterfront, watch waves crash against the rocky shore at Rafe’s Chasm, or wander the almost impossible quaintness of Annisquam village.
And if you need some help finding your way, locals will be happy to oblige. Just be prepared for answers referencing lesser-known landmarks or former residents, Curcuru says.
“Don’t be afraid to ask for directions,” he says, “but the answer you get might be weird.”
Places to Eat
Oak to Ember
Wood-fired meats and fresh seafood are the focus at this relaxed-but-modern waterfront spot.
1606 Restaurant and Oyster Bar
Sip a cocktail on the waterfront deck, slurp shellfish at the oyster bar, or settle into a booth for a luxe dinner.
Talise
The farm-to-table fare is over-the-top delicious, but the vibe is casual and welcoming at this waterfront eatery tucked away in Annisquam.
Tonno
Italian-inspired and heavy on the seafood, Tonno serves up entrees, pastas, and specials using fresh, local ingredients.
Yella
Enjoy creative, Mediterranean-infused flavors on a breezy deck overlooking scenic Gloucester Harbor.
Holy Cow
End (or start) your day with award-winning ice cream in flavors from perfectly simple vanilla to creative seasonal concoctions like wild blueberry pie.
The Cut/ Little Sister
Grab tickets to a musical performance or comedy show, or just drop in to play some pool and enjoy one of the area’s best burgers from pop-up Little Sister.
thecutlive.com, littlesisterburger.com
Things to Do
Cape Ann Museum Green
A four-acre campus featuring rotating exhibits, an historical home, outdoor sculpture, and a recreated Wampanoag wetu.
Gloucester Stage Co.
Take in a professional performance at the intimate, acclaimed theater.
Eastern Point Lighthouse and Dog Bar breakwater
Stroll along the 0.4-mile granite breakwater then turn around for postcard-perfect views of the historic lighthouse.
Ravenswood Park
Ten miles of trails wind through wetlands, over rocky hills, through shaded forests, perfect for hiking, picnicking, and dogwalking.
Rocky Neck
The country’s oldest working art colony includes colorful galleries and studios, amazing views, and the Salted Cod Arthouse, where you can sip wine, enjoy a snack, and shop the work of local artists.
Schooners
Whether you choose the Ardelle, the Adventure, or the Thomas E. Lannon, a Gloucester schooner ride merges history and adventure.
maritimegloucester.org, schooneradventure.org, schooner.org
Stacy Boulevard
This half-mile promenade along the harbor is home to the iconic Fisherman’s Monument and lush garden beds throughout the spring and summer.
Places to Shop
The Bookstore of Gloucester
The friendly, book-savvy staff will help you find the perfect volume (Nicole is a magic-worker) on the packed shelves in this charming shop.
Goodlinens Studio
Shop for beautifully designed home goods from the eponymous linen dishtowels to a curated selection of kitchenware.