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Marblehead is picture-perfect any time of year, with its historic houses tucked onto winding streets along a beautiful working waterfront on Marblehead Harbor. But during the holiday season, when the town is decked out with wreaths, evergreen boughs, and twinkling lights, it takes on a magic that’s hard to find anywhere else. “It’s so beautiful to walk around,” says Cassie Sturdivant Watt, Marblehead resident and owner of Mud Puddle Toys. “It’s got this beautiful, old-fashioned vibe, especially if it’s just snowed.”

The holiday season in Marblehead kicks off each year at the beginning of December, with a multiday Christmas Walk that features an artisan market, gingerbread festival, Christmas tree lighting at Grand National Bank, music, and, of course, the arrival of Santa and Mrs. Claus by lobster boat in Marblehead Harbor. “It’s an amazing tradition,” says Katherine Koch, executive director of the Marblehead Chamber of Commerce, which runs the Christmas Walk. “Not every town gets to have Santa Claus come in on a lobster boat.”

A festive month

Although the Christmas Walk happens in early December, the cheer continues throughout the entire holiday season in Marblehead. “Just because the Christmas Walk happens at the beginning of December, doesn’t mean that the festivities stop for the rest of the month leading up to the holidays,” says Koch. For instance, simply walking through Old Town Marblehead is enough to put even the Grinch in the holiday spirit, thanks to small, mom-and-pop shops; quaint, walkable streets; and a cozy feeling of neighborly togetherness that exudes Hallmark movie vibes.

It’s tailormade for a day of picturesque strolling and shopping, then stopping to warm up with a seasonal cocktail by a cozy fire at a place like Harbor Light Inn, which welcomes overnight guests and day-trippers alike in its tavern. “December is one of our most popular months in the tavern,” says owner Carolyn Pyburn, who adds that the seasonal cocktails, like chocolate peppermint martinis and Champagne spiked with drinkable glitter, add to the merriment. “We go over the top with decorations. It feels so festive in the inn.”

Those who do stay overnight in December can include a Christmas package with their stay, adding a small lighted tree and a box of Sweet Sloops from Harbor Sweets to their room, along with holiday cocktails in the tavern.

Odes to the sea

Given Marblehead’s location, it’s not surprising that many of the town’s Christmas and holiday traditions revolve around the ocean in some way. “Wherever you are in downtown Marblehead, the water is never far away,” says Watt. Not only is Marblehead Light at Chandler Hovey Park lit up for the season, but local businesses add their own seaside flair to the town’s décor.

For instance, First Harbor Company, which creates handmade, nautical rope wreaths, launches a traditional wooden boat with a lit and decorated Christmas tree into First Harbor. It floats and glows on the water from December 1–31, says Tom Peach, who owns First Harbor Company with his wife, Samantha. “It’s gotten to be something that people want to take pictures of,” says Peach, a lifelong Marblehead resident and descendant of one of the town’s founding families.

Over on land, Mud Puddle Toys builds, lights, and decorates a lobster trap Christmas tree outside the store and also installs “Santa’s mailbox,” encouraging little passersby to send their letters to Santa, which he answers on Christmas Eve. The store also hosts caroling outside every Saturday leading up to Christmas, Watt says.

Jennifer Uhl, chairperson of the Marblehead Cultural Council, also notes that many of Marblehead’s most beautiful sights are available just by walking around, from reading the historic plaques on the historic houses, to enjoying the decorations, to taking in the incredible ocean vista at Fort Sewall. “That’s the most beautiful place in the world, and you get that panoramic view,” she says. “You’re at the edge of the earth.”