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Getting to Marblehead is not intuitive. There is no straight road that delivers visitors simply into town. You’ll need to wind through the bustle of Salem, or along the residential shoreline of Swampscott, or maybe zig-zag through Lynn. You definitely want to have Waze pulled up and ready to consult as you travel. 

When you arrive, however, you’ll discover why so many people make the effort to navigate their way to town. Marblehead offers an immersion in both history and seaside living—and the many ways the two intersect—that is rarely found, even in a region with as deep a sense of the past as the North Shore.

“You kind of feel like you’re stepping back in time,” says Melissa Stacey, co-owner of Discover Marblehead, a local business dedicated to promoting the town. “It’s a small, quaint, historic seaside town.”

The water continues to shape the town, drawing in recreational sailors who found beauty and practicality in the town’s sheltered harbor. “People came to Marblehead because it had this protected harbor,” says Pam Peterson, a member of the Marblehead Historical Commission. “That determined its history to a large extent.”

Chandler Hovey Park

The town’s easy distance to Boston has also made it a popular home for commuters, and its stunning views and quaint downtown attract countless visitors. Today, a walk through town makes evident the way the past and present unite in contemporary Marblehead.

“You get a little bit of everything: the water, shopping, history,” says Stacey, a third-generation resident.

Several places in town allow visitors to enjoy the natural splendor of Marblehead’s location. At the northern tip of Marblehead Neck, an almost-island connected to the mainland by a narrow isthmus, Chandler Hovey Park affords views of the harbor to one side and a sweeping panorama of the open ocean to the other. Gerry Island and Crowninshield Island are accessible by foot only at low tide but offer intrepid visitors beautiful terrain and educational displays about the island’s history. 

“That is the hidden secret that nobody should miss,” says Amy Berenson, president of the Marblehead Business Network.

Back in town, historic Fort Sewall is still home to bunkers and rooms used to detain prisoners, combining sobering history with stunning vistas. 

“It’s a beautiful promenade that’s surrounded mostly by water, and the views from there are really spectacular,” says Berenson, who has lived in Marblehead for 32 years. “On a summer day to go out there and see the sailboats sailing around and the motorboats buzzing, it’s just breathtaking.”

A pasta dish at The Landing | Photograph by Brian DeMello

In town, even a short stroll will take you past some of the dozens of well-kept historic houses that characterize Marblehead: The town is said to have one of New England’s highest concentrations of homes from the 17th and 18th centuries, a statistic that is easy to believe as you wander the town. 

Step even further into the past by exploring the town’s “secret passageways,” nearly hidden historic paths and alleys, still open to the public, that were used by long-ago residents to travel efficiently through town. A map of these public rights of way is available on the website of the Marblehead Conservancy. 

As you wander, take time to explore the small, sometimes quirky, independent shops that are the hallmark of Marblehead’s retail scene. Stock up on greeting cards and wrapping paper at Scribe, take home a reminder of the seaside from Sweetwater & Co., or find a gift for your favorite little ones at Mud Puddle Toys. 

When it’s time for a break, Marblehead has plenty of options for food and drink. If the ocean has inspired you, The Barnacle is one of the town’s favorite places for casual seafood meals. At The Landing, the menu is full of globally influenced choices, and the tables offer sweeping views of the harbor. If it’s a cocktail you crave, try the Mai Tai Lounge, where there are eight versions of the eponymous beverage to choose from, as well as dozens of other delicious concoctions. 

Your experience will leave you eager to find your way back to Marblehead soon.