Part holiday-shopping heaven, part old-fashioned block party, the island’s annual Christmas Stroll brings locals and visitors together for a holly, jolly weekend. 

By Tracey Minkin
December 04, 2014

It’s a bracing winter day on Nantucket, and the narrow wharf is packed with people—stomping their gray Hunter boots on ice-sheened cobblestones, tightening crimson wool scarves, swapping jokes over clutched cups of coffee, and gripping the mittened hands of bundled-up, cherry-cheeked children. Everywhere, bobbing atop this sea of humanity like gulls on a swell, there are hats. Yes, sensible knit caps for a cold New England day, but also Santa hats, elf hats, reindeer antler hats, pirate hats, fedoras festooned with holly and berries, and headbands anchoring tiny, teetering stacks of presents. And while this crowd may look flamboyant compared to the Nantucketers who've congregated at this very spot for hundreds of years to welcome their seamen, scallopers, and lobstermen home, they are doing what has always been done here: eyeing the horizon.

Because they are waiting for Santa, and he's coming by boat.

Such is the buoyant bonhomie of Nantucket's Christmas Stroll. Created 41 years ago to lure shoppers across the water for a burst of economic goodwill before shuttering shops for the long winter, this holiday-themed weekend has evolved into much more than a promotion. While the island's hundreds of independent businesses do welcome close to 12,000 shoppers who come to hunt and gather its distinctive, upscale wares, to bed down in its luxurious resorts and inns, and to sample its world-class restaurants, Nantucket also transforms into one big, jolly block party full of old-fashioned fun. It's two parts Christmas Carol, one part Mardi Gras, with a twist of Melville. And it's no wonder that for many, The Stroll, as it's called, is an annual pilgrimage without which the holiday season cannot properly begin.

"It gets you kick-started into the whole Christmas thing," Dale Albright tells me earlier that morning over breakfast. Albright and his wife are devoted strollers—back for the 14th year in a row, they've carried on a long-distance love affair with the island from New Jersey since their honeymoon. "We fell in love with the place," Dale says. Dorothy, meanwhile, geared up in tartan trousers and a luxuriant cream-colored turtleneck, eyes her extensive, handwritten list. She'll do all their holiday shopping here, she says. Like a thoroughbred straining at the gate, she's anxious to get going.

For some, this weekend will be a giddy gauntlet of shopping with little pause. For most, though, it's a browser's delight. Every block of Nantucket's historic downtown is lined with extravagant shop windows, gaily decorated doorways, twinkly lights, and legions of small fir trees along the narrow sidewalks, each decorated by local businesses and organizations.

The shops throw their doors open in welcome. Everywhere you go, someone is giving away free cups of cider, sips of wine, or nibbles of chocolate. Main Street—a cobblestone expanse that fills with vehicles during the summer months—today fills with milling folks who linger for brass band serenades, Christmas carols, and photo opportunities with locals who've come out in their best holiday regalia. That fellow with the walrus mustache wearing the barn coat and wire-rimmed spectacles who has a Christmas wreath crowning his head like an L.L.Bean version of the Ghost of Christmas Present? He's patiently posing and has probably been Facebooked, Instagrammed, and Pinned more times today than Taylor Swift.

And there are dogs—lots and lots of dogs. Labradors and golden retrievers herald their movements with sleigh bells jingling on their collars. Italian greyhounds and French bulldogs pose aristocratically in their tight-fitting sweaters. It's a parade at every level. Even the vintage pick-up truck parked nearby sports an enormous Santa hat on top of its cab.

"When you walk down the street, everyone you see has smiles on their faces," says Eric Schoenfeld, another New Jerseyite who is here for his first stroll with his wife, Barbara. "And it's so easy to meet people." Indeed. In just a day, you'll be introduced to locals from every strata on the island, from a young fashion entrepreneur whose hand-sewn silk holiday fascinators are flying off the shelves at a local boutique to the patriarch of Young's Bicycle Shop (where a Christmas tree made from bike fenders sparkles beside a video of a roaring fireplace). There are artists and surfboard makers, carpenters and real estate agents. There's a couple who grew up playing at the same Nantucket beach more than 40 years ago. They both moved away and fell completely out of touch. This year they rediscovered each other, and love, back on the same small island.

Meanwhile, in the peaceful sanctuary of Nantucket United Methodist Church, Sara Jones has collected hundreds of crèches and put them carefully on display for the weekend. Calling the exhibition "No Room at the Inn," Jones takes donations at the door to help provide food and shelter, plus heating fuel assistance, for islanders in need. It's a sweetly gentle reminder that Nantucket remains a place called home by many—and that's what makes this holiday celebration of visitors and locals so unexpectedly heartfelt. It makes a weekend on a sandy crescent, less than 30 miles offshore and laid open to icy gales, downright warm.

Back at the wharf, a Coast Guard cutter has pulled assuredly to dock. With a heavy scallop shell trimming the ermine of his cap, Santa steps ashore like a festive holiday Neptune. Children finger his rich, red coat, and he beams down at them. With Mrs. Claus at his side, he draws the crowd along with him up the cobblestoned way, toward more revels and more wonder, back into the heart of Nantucket.

Nantucket Christmas Stroll 2015 is December 4-6. For more information, call the Nantucket Chamber of Commerce at 508/228-1700, or visit

How to Get Here
Whether you're enjoying The Stroll for one day or all weekend, it's an easy, speedy ferry ride from Hyannis, Massachusetts (, or a quick flight on Cape Air from Boston, New York, and other airports (

Where to Stay
The sophisticated welcome of the White Elephant Hotel and Village Residence offers myriad pleasures (and all-day coffee and cookies) just a five-minute walk from Main Street. Rates start at $195; 508/228-2500 or The Union Street Inn is elegantly friendly, features one of the best breakfasts on the island, and is five minutes from all the action. Rates start at $349; 508/228-9222 or

Where to Eat
When it comes to dining, Nantucket provides like almost no other resort town. Smart strollers do lunch without lines at Brotherhood of Thieves by patronizing the lively (and heated) beer garden out back; 508/228-2551 or For dinner, Proprietors Bar & Table is the high-profile latest project from Orla and Michael LaScola, whose American Seasons is a Nantucket star; 508/228-7477 or Closer to the water, Lola 41 specializes in delicious sushi and other foods from the latitude of 41 degrees; 508/325-4001 or The oysters and cocktails at Cru, at the end of Straight Wharf, are glorious any time of day or night; 508/228-9278 or

Photos: Reena Bammi