Nantucket Christmas Stroll combines New England charm, upscale extras

The Claus’ arrive in Nantucket for ChristmasCary Hazlegrove | NantucketStock

Saturday after Thanksgiving — a big day on little Nantucket Island. That’s when Santa Claus and the missus bid a fond farewell to the sleigh and reindeer, sail into the historic harbor aboard a Coast Guard cutter, clamber onto an antique fire truck and clatter up Main Street’s cobblestones, waving at cheering grown-ups and wide-eyed children. Laughing all the way, of course.

The arrival of the right jolly old elf highlights Nantucket’s “Christmas Stroll,” a three-day celebration of all things Yuletide on this oh-so-charming, exclusive Massachusetts island better known for its warm, sunny summers, pristine beaches, upscale amenities and year-round preppy persona.

The Stroll began in 1973 when merchants and business leaders dreamed up a three-hour seasonal event on the Friday after Thanksgiving to prevent islanders (and their wallets) from escaping to nearby Cape Cod for their holiday shopping. It soon turned into a full-blown celebration, and the word went forth: Nantucket’s not just for summer anymore.

Santa arrives in Nantucket for Christmas
Santa arrives in Nantucket for ChristmasPhoto by


“Quaint” doesn’t even begin to describe the enchanting, snow-globe appeal of the weekend. Hundreds of decorated and illuminated seven-foot-tall Christmas trees line the streets downtown, lorded over by a twenty-foot pine at the top of Main Street that magically talks to passersby. There’s an “Ugly Sweater” contest, ice carving displays, craft shows, musical performances, tours and exhibitions, and on and on. Shopkeepers serve wine, hot chocolate, tea, mulled cider, fruitcake and holiday cookies as visitors check out local crafts, books, clothes and other holiday gift possibilities. Restaurants and bars throw open their doors with all kinds of mouth-watering offerings, including local aquatic delicacies, wines and beers.

Children line downtown’s Broad Street, eagerly awaiting a chance to meet Santa Claus in the Jared Coffin House. His temporary holiday home is a magnificently restored three-story mansion, built in 1845 by one of the town’s wealthiest shipowners, and now an upscale hotel. Bundled up in brightly colored yarn hats, fleece jackets and boots, the kids clutch candy canes in mitten-wrapped hands and sip hot chocolate ladled out by hotel staff. Their twinkly eyes dance with excitement as carolers in Victorian costumes sing. It’s enough to make even an old sea dog misty.

The popular “Holiday House Tour” allows visiting peasants to admire historic downtown homes, all bedecked for the season.

Jared Coffin House, owned by Nantucket Island Resorts
Jared Coffin House, owned by Nantucket Island ResortsCary Hazlegrove | NantucketStock


The big social event, however, is the “Festival of Trees Preview Party,” sponsored by the Nantucket Historical Association at their showcase Whaling Museum. Transformed into a winter wonderland, stuffed with community-crafted trees designed by local merchants, nonprofit organizations, artists and school kids, it’s the hottest ticket in town — seriously — and sells out way in advance.


Stroll’s Haute Hotels

Island accommodations abound, but we like the casually elegant, blue-chip White Elephant, a five-minute walk from the town’s center. Located on Nantucket Harbor, the White Elephant has been a favorite island retreat since the 1920s, when the rich and feisty Elizabeth Temple Ludwig was planning a new harborside hotel. Fellow islanders sneered, predicting that the hotel would be a hopeless white elephant. Defiantly, that’s what she named it.

The joke was on the sneerers — the White Elephant became an enduring destination. In 1999, new owners Stephen and Jill Karp of Nantucket Island Resorts bought and extensively renovated the property. Today, the iconic gray-shingled hotel boasts 67 luxurious guest rooms, suites, cottages, and two luxury lofts. Rooms are tastefully appointed with the work of local artists, and the beds are bedecked with Italian linen legend Pratesi sheets. There’s a small but sunny library where port and cheese are served starting at 4 p.m., as well as an exercise room, business lounge, spa and a relaxing harborside lawn area. Brant Point Grill, one of the best places to dine on the island, features steak, lobster and seafood of all kinds, as well as a waterfront view.

Nantucket in Christmas
Nantucket in ChristmasPhoto by


Guests who book the top accommodations get complimentary use of a 2017 BMW for the duration of their stay, as well as bikes to pedal around. (We’ll take the BMW, thanks!)

For the best seat in the house for Christmas Stroll, consider 32 Main Street White Elephant Lofts. On the second floor of a brick building above a retail shop, there’s an uber-chic, 2,500-square-foot three-bedroom loft apartment with wood floors, a gourmet kitchen, dining table for eight and a huge picture window overlooking Main Street and all the holiday festivities.


The Other Three Seasons

While Christmas Stroll is clearly a singularly delightful experience, anytime on this tiny spit of land — three and a half by 14 miles – is pretty spectacular. Spring starts the onslaught of vacationers and in summer months, the island’s population swells from 10,000 to about 60,000. Yet the islanders seem to absorb all the hubbub with casual aplomb. Tourism is their business, after all.

For summer and shoulder-season stays, another hotel option is the Wauwinet, a historic 31-room enclave named for the Wampanoag Indian chief who presided over the island in earlier days.

Christmas in Nantucket
Christmas in NantucketCary Hazlegrove | NantucketStock


Exuding whimsy and charm, the Wauwinet is Nantucket’s only member of Relais & Châteaux, an association of more than 550 independent hotels and restaurants around the world with the goal of preserving and promoting local cuisine, traditions and hospitality. It’s also home to the award-winning Topper’s Restaurant. Zagat understandably loves the place. Chef Kyle Zachary focuses on local ingredients and procures produce from island farms, shellfish from local waters and meats from sustainable sources throughout New England. The locally harvested Retsyo oysters, cultivated a mere 300 yards away, are sublime, as is the chowder — tawny, brimming with whole clams, oysters and mussels.

And then there’s Topper’s wine director Craig Hanna. He’s the Daniel Day-Lewis of Wine Spectator’s Grand Awards, but also a regular guy you can have a beer with. For 32 seasons, he’s patiently assembled a 24,000-bottle cellar of stellar selections from Burgundy, California and Italy. When he comes to your table and offers to pair wine with your meal, sit up and pay attention — you’re in the hands of a master.

An absolute must — the desk will arrange a tour with cheerily enthusiastic Captain Rob, whose knowledge of Nantucket lore is inexhaustible. Two hours with him as he masterfully shifts the Wauwinet’s three-on-a-tree 1947 Chevy Woodie will turn you into an island expert, and he’ll point out unforgettable photo ops, too.

Things fall off quite a bit come autumn, however. Many shops, inns and restaurants close for the season, with hand-scrawled signs taped to their windows — “See you in March!”

But seasoned travelers willing to take a chance on fall’s meteorological vicissitudes are often rewarded with sunny days, nippy nights and spectacular foliage. Just this past October, in fact, Nantucket’s mornings were actually warmer than Fort Worth’s. And there are tons of photo ops during the annual cranberry harvest and autumn’s unmatched raiment of rich colors.

Spring is also a great time to visit, starting with April’s Daffodil Festival, which is a lot more promising than it sounds. Themed activities happen across the island, topped off with a vintage car parade up Main Street that treks out to the unbearably picturesque village of Siasconset (or as the locals say, ’Sconset) on the island’s east side for a big tailgate party where everyone is decked out in bright yellow togs.

Mark your calendars – 2018’s Daffodil Festival is the 30th anniversary of the Wauwinet under current management and they’ll blow out the event with an “Apres Tailgate Party” on the lawn with raw bar, wine discounts, lawn games and complimentary transportation from ’Sconset to the party.


Christmas Stroll 2018

Planning ahead is always key to a Nantucket escape.

Christmas Stroll weekend now attracts nearly 12,000 domestic and international visitors. It’s just part of the Chamber of Commerce’s successful month-long “Nantucket Noël” program, designed to attract tourists (and their wallets) with New England charm.

Santa arrives in Nantucket
Santa arrives in


If you are thinking about a Stroll visit in 2018, you’ll want to make your reservations early — like, now. Accommodations and restaurants fill up fast.

Of course, they do. After all, if you can’t get sentimental about living in a Christmas snow globe, with sparkly snow, fir trees and hooded carolers singing you home, you really should re-examine your priorities.


Nantucket’s Whaling Past

Bucolic as Nantucket is, everyone, and we mean everyone, will anxiously inquire as to whether you’ve taken in the National Historical Association’s Whaling Museum. A negative response elicits a sorrowful head shake and a plaintive plea to “go, just go, you won’t be sorry.”

You won’t. The informative displays explain Nantucket’s economic rise and abrupt fall as hunters and processors of spermaceti oil, the elixir that illuminated the world before the advent of petroleum and electricity. Prior to Nantucketer’s maritime adventures, sputtering and smelly tallow candles lit western civilization. Whale oil, however, burned bright and clear. But residing as it did in the head cavities of sperm whales meant that hunters had to venture far afield into the Atlantic and later the Pacific in wooden sailing ships to kill the beasts, then extract their oil and render their fat in a grisly and distasteful process that offends our modern sensibilities.

Nature, however, got the last word. Presaging the whaling era’s decline, the Nantucket-based Essex sailing ship was rammed and sunk by an understandably peevish bull whale in the Pacific. The crew’s excruciating experience became legend, inspiring Herman Melville’s Moby-Dick. (Nantucket resident Nathaniel Philbrick recounts the real-life tale in In the Heart of the Sea, a book that then inspired the 2015 Ron Howard-directed film of the same name.)

An interesting aside — in 1998, a dying sperm whale beached itself on the eastern end of the island. Tools from the museum were brought out of retirement, sharpened and put to work. When the whale died, it was drained of as much oil as possible (hundreds of gallons remained), and the carcass was placed in a cage and sunk offshore, much to the delight of crabs and other ocean denizens, who feasted on it for six months. The bones emerged sparkling clean and, after judicious chemical treatments, are now impressively displayed in the museum’s Gosnell Hall.

Emmy award-winning filmmaker Ric Burns, Ken’s younger bro, captures all of this in the museum’s signature film, Nantucket. It’s all there — the island’s unparalleled beauty, as well as its turbulent whaling history.


Nantucket Fast Facts

  • “ACK” is the Federal Aviation Administration’s designation for Nantucket Memorial Airport – the call letters refer to the original airstrip called “Ackerman Field” and provide much hilarity on T-shirts, hats, bumper stickers and other touristy stuff.
  • “Nantucket” is the name of the town as well as the island and harbor. Makes it sort of hard to get lost.
  • The island encompasses 48 square miles — erosion is a big problem and some scientists predict Nantucket will be history in 400 years.
  • There are no campgrounds, traffic lights, neon lights or fast-food chains on the island. Almost 30 percent of the island’s total land area is protected open space owned by the Nantucket Conservation Foundation.




If You Go

Nantucket Island Resorts operates the White Elephant, the White Elephant Village, the Wauwinet, the Jared Coffin House, the Nantucket Boat Basin and The Cottages.

The White Elephant was awarded the Forbes Travel Guide Four-Star rating this past February and was voted No. 6 in the “Best Waterfront Hotels” category as part of USA TODAY’s 2017 “10 Best Readers’ Choice Travel Awards.” Recently, Condé Nast Traveler’s 2017 “Readers’ Choice Awards” named the Cottages at the Nantucket Boat Basin, White Elephant, White Elephant Village and the Jared Coffin House to the “Top Hotels in New England” category, and the Wauwinet was honored in the “Top Resorts in New England” category.

White Elephant: 50 Easton St., Nantucket, MA 02554, (508) 228-2500

Rates: $225 to $695 (Lofts run $3,200 per night during Christmas Stroll 2017, $1,995-$4,295 per night the rest of the year.)


The Wauwinet: 120 Wauwinet Road, Nantucket MA 02584, (508) 228-0145, $195-$595


Nantucket Historical Association and Whaling Museum:

The 2017 Festival of Trees opens to the public on Friday, Dec. 1, 2017, with special extended museum hours from 10 a.m to 8 p.m.

Nantucket Chamber of Commerce:

Event Calendar:
Brian Melton admits to being smitten with Nantucket’s bountiful charms. Especially the chowder.





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