Gloucester is best known for two things: fishing and beaches. And it’s true that the city’s fishing industry and tourist appeal are two major pillars of its economy and identity. Any Gloucester resident, however, can tell you that there is far, far more to the city than its reputation for quality seafood and relaxing beach days.
“One of the things I love most about Gloucester is that it is full of hidden gems,” says city councilor Jen Holmgren, who has lived in Gloucester for most of her life. “There are dramatic vistas literally around every corner it seems.”
Settled in 1623, Gloucester is one of the oldest communities in Massachusetts. It was a fishing town from the very beginning, and the industry remained the lifeblood of the city for centuries. Over time, though, the culture of the place expanded and deepened. In the 1800s and 1900s, renowned painters including Winslow Homer, Edward Hopper, and Mark Rothko flocked to Gloucester, drawn by its striking beauty, working waterfront, and unique light. At the same time, the area was increasingly popular as a summer retreat for wealthy families from Boston and New York.
Today, fishing boats still dock in Gloucester and tourists still pour in every summer, but the city has become a multifaceted destination with a seemingly endless supply of unique culture, diverse food, compelling art, quirky nooks, and stunning natural beauty.
Like the rest of the state, Gloucester has been grappling with the COVID-19 pandemic. Many stores have closed temporarily, while others have been limited to telephone orders and curbside pickups. The community, however, is doing what it can to support its valued local businesses, buying books, toys, pizzas, and pastries to help them get through these challenging times.
Local fishermen organized a drive-through pop-up event selling haddock and scallops, and the line for the seafood stretched around the block. Students who depended on free school meals can pick up a bagged lunch and breakfast every day at pick-up sites around the city, and the Open Door food pantry has served hundreds of families in need with curbside pickup meals and groceries.
“In the business community the morale has been really good,” says Mayor Sefatia Romeo Theken, speaking on local public access television network 1623 Studios.
At the Beauport Hotel, which closed temporarily, planning is underway for post-coronavirus events. A new multifaceted wellness initiative will have the hotel hosting regular yoga classes, open to the public and to guests, on its oceanfront deck. The hotel is also excited to have a new chef in the kitchen, who is working on a spring menu to unveil when the property is able to open again.
“We are still planning and still hoping it is going to be a wonderful summer,” says hotel spokeswoman Jeanne Hennessey. “We just can’t wait to open our doors again.”
The return of freer movement and the lifting of business restrictions will hopefully restore activity on the working waterfront and the small businesses that line Main Street. Far from the malls and the big box stores, Main Street’s shops and eateries give visitors a chance to find a one-of-a-kind gift or eat a special meal. There are bookstores, vintage boutiques, gourmet shops, and art galleries.
Date of Settlement
Date of Incorporation
41.5 square miles
Median Household Income
Artist and author Virginia Lee Burton, frozen food pioneer Clarence Birdseye, inventor John Hays Hammond, Jr., painter Winslow Homer, early feminist and writer Judith Sargent Murray, Olympic ice hockey coach Ben Smith, college founder Roger Babson, musician Willie Alexander
As you wander, keep your eye open for art—several murals line side streets and alleys, and there are even spots where small mosaics have been created to fill holes in the sidewalk. Just a little off the main drag, City Hall features murals painted as part of the New Deal following the Great Depression, and the Cape Ann Museum immerses guests in the art, history, and culture of the region.
“It’s almost like going into a different world,” Holmgren says.
Hungry? Sandpiper Bakery, one block off the main drag, sells croissants that will transport you to Paris. For a heartier lunch, visit Virgilio’s, a third-generation Italian bakery shop, where loaves of fresh semolina bread line the windows and locals crowd in for sandwiches piled high with flavorful imported meats.
About a mile outside of downtown, sits Stage Fort Park, easily recognized by the towering rock that looms over the park’s rolling green hills. Wander past the playground and follow a rocky path toward the water, and you will discover Half Moon Beach, a never-crowded crescent of sand edged by rocks and trees that just might be the city’s most charming beach. Pick up the trail again on the other side of the beach to explore a network of wooded paths to take in views rarely experienced by visitors.
East Gloucester, an arm of land stretching south from the heart of the city, is largely residential, but offers a few unexpected delights. The most obvious of these is Rocky Neck, a working art colony since the 19th century, where colorful, quirky galleries line the streets and every corner reveals a new picturesque view of the city’s working harbor. Around the corner, the Gloucester Stage Company produces professional theater in an intimate setting, and up the street, Duckworth’s Bistrot serves up lobster risotto, banana cake, and other acclaimed fare.
Drive or stroll up nearby Eastern Point and view stately mansions built largely as second homes for wealthy summer visitors in the late 19th and early 20th centuries. One of these, Beauport, the Sleeper-McCann house, is open to visitors; each room is impeccably decorated to a different theme, featuring detailed murals, stunning furniture, lush gardens, and lots and lots of color.
To discover breathtaking water views that are not on most itineraries, follow Route 127 north from Route 128. The road winds next to the inlets and coves of the Annisquam River, and then along Ipswich Bay, serving up dramatic glimpses of rocky shoreline, moored sailboats, and open water. Cross the stone bridge and turn down into the village of Annisquam to get quite literally lost in its maze of narrow roads and quaint shingled homes. Continue up the main road to Lanesville, a neighborhood known for its expressiveness and eccentricity; keep an eye out for the yellow road sign warning “Beautiful Dreams Ahead.”
And there is, of course, so much more to explore: the trails in the abandoned 17th-century settlement at Dogtown, the evolving village of Magnolia, the stunning views at the Tompson Street Reservation.
“You could live here for decades,” Holmgren says, “and still go down streets you never even realized were there.”