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I had one job: find the perfect pair of wine glasses. Only two, enough to wrap and stow in a carry-on, and this was my wife’s charge to me on Nantucket. I was flying to the island for its famous Christmas Stroll, and if I couldn’t secure just that swag, she knew it would be because I’d been waylaid by fun.

Dear, you needn’t worry—I found both.

Though the famously-secluded whaling village is beloved as a summer destination, Christmas begs a second look, since it’s developed its own fizzy kind of charm, particularly during the Stroll. Here’s the story: sometime in the early 1970s, just thirty miles across the Nantucket Sound, the Cape Cod Mall in Hyannis opened to the public. All those wonderfully crafty, mom-and-pop stores on Nantucket that depended on profligate holiday shoppers to help them past the shoulder seasons panicked, and understandably so. Locals gathered to devise a means of keeping folks from fleeing to the mainland, choosing the soullessness of a corporate shopping mall—this was during the 1970s, mind you, when malls were just the place to be—and hence, the Stroll was born.

How to describe it? A three-day party, outdoors and in, featuring inventive cuisine (oyster tacos in Nori paper, at Nautilus); speakeasy-style bars with excellent Chateau Margaux (Oran Mor, tucked above an art gallery); a raucously late-night brewery party or two (try Cisco’s); dozens of open houses, toddy tastings, ugly sweater competitions, craft shows, history tours, a Tree Festival, a Miracle on 34th Street-quality Santa Claus who rides into town on a special ferry, and a general atmosphere of people festively defying Seasonal Affective Disorder. Ferries go back and forth to the mainland until all hours; shop windows are ablaze in festive approximations of Fifth Avenue swank; nearly every restaurant and café stays open extra late throughout, as do the shopkeepers, gallery owners, booksellers, barmen and baristas, all welcoming crowds with small-town considerateness and boutique Christmas shopping you won’t find at Williams-Sonoma. The festooned main square becomes a sketching by Boz for A Christmas Carol, a scene of holiday merriment out of a distant century: shingles bedecked, music jingling, evergreens alight, and everywhere you look, a satisfied Fezziwig smile.

My first morning, a stranger passed me a shot of whiskey, exclaiming, “You look cold!” We clinked glasses: both of us had the twinkle-eyed, rubbery-red faces of people who look for any excuse to run around outside in winter sunlight. “Wine glasses?” I asked, and he sent me towards Christopher’s, on Washington Street. Up the cobblestones, a brass duo was performing a yeoman’s job of God Rest Ye Merry Gentlemen and only after I downed the shot did I realize it was a steaming-hot shot of lobster bisque. It did the trick.

Despite what you may have heard, Nantucket is a superb town to simply get lost in, wandering the many crooked, Lilliputian streets that twist away from the main square, and where it’s often hard to tell museums from private residences, as I learned when I walked into a home and began admiring the china. I spent a contemplative quarter of an hour at St Paul’s Episcopal, where visitors often peruse the gorgeous Tiffany windows of stained glass and pay their respects at the candle-tribute to Mister (Fred) Rogers, a beloved longtime Island resident. Downstairs was an honest-to-God, old-fashioned church basement potluck and craft fair, where I bought a stitched sampler and two cups of the best oyster stew I’ve ever had. (And no one asked me to join a study group). One evening I happened into the Dreamland theater, where a Christmas performance was underway by the actual Vienna Boys’ Choir, who sent Il es né le divin Enfant floating, delicately as snowflakes, out the front doors.

Each day of the Stroll, however, you somehow always find your way back to the square, its bustle and blaze and warmth, like hands to a hearth.

I recommend finding your way to the White Elephant Hotel, up the slightly quieter, northwest flank of the waterfront, a sort of elegant cuff to Nantucket Bay’s wharf where you’re not in the thick of revelers, but a mere three blocks away. The riverfront gets busy, but the Elephant retains a crucial serenity (excepting its excellent restaurant, the Brant Point Grill, which is seemingly always hosting a garden party, even in freezing cold). The White Elephant properties form a presidential-style compound, including the Inn, the Village, and the Residences—a variety of rooms, suites, and apartments for wayward Christmas pilgrims and families of all sizes. I enjoy bed-and-breakfasts as much as anyone, but creaky charm and spartan amenities become something else entirely in colder weather. The Elephant is modern, cozy, and diligently looked after by a professional staff of impeccable courtesy and skill. Special mention must be made for the luxurious bedding, a souvenir which, it turns out, nearly all guests ask the front desk if they can steal before check-out. Downy white, homespun Italian cotton (by Rivolta Carmignani), it has become as much of a signature of the property as the little ivory-white elephants stitched into the throw pillows. And yes, it is available for purchase. Just a stone’s-throw south of the famed Brant Point Lighthouse, the White Elephant is an ideal spot for romantic nesting, family gift-exchanging, or at the end of the day, simply taking in a view of those glorious, candy-pink December sunsets on the harbor. Everyone deserves to experience a Stroll, at least once, and snag a room at the Elephant before the season ends—they board up for the winter.

Hearing this, I was put in mind of the following story.

Years ago at a holiday party in Manhattan, I asked the five-year-old son of the host—a cherubic, blond little guy—what first came into his head when he heard the word Christmas. He grinned and whispered, “The mall.”

Oh, you poor thing, I thought.

There’s something about this season that turns every child into a born sensualist. So after spending three delightfully chilly days exploring the charms of the 44th Nantucket Christmas Stroll, I’ll admit I was more than a little jealous of all the kids I saw, drinking in this absolutely unique, picturesque scenery, creating sense-memories that would tug at their hearts and provide a benchmark for how to “do” Christmas the rest of their lives. Frankly, I wish someone would have ferried me here when I was a kid. Alas, I settled for adult pleasures: Oran Mor’s cocktail list, chilled oysters at Cru. Those perfect wine glasses turned out to be gold-crested goblets, and meanwhile I managed to grab a handful of other gifts I will keep for myself, things I’d be hard-pressed to find elsewhere, like an ink by local artist John Lochtefeld, a scrimshaw-inlaid knife and handmade leather Dopp kit from Craftmaster’s, as well as the bedding at the White Elephant, of course. I told the hotel staff, next Christmas, in all honesty, I’m skipping the malls and bringing the wife.


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