Sandy shores and warm breezes bring beach lovers to Nantucket each summer; but if you hop the high-speed ferry and ride the winter winds to the island in December, you’ll be rewarded with the undeniable charms of Nantucket Noel. This month-long celebration is a throwback to an old-fashioned New England holiday, with carolers singing, scallop-shell Christmas lights twinkling and summer’s favorite seasonal restaurants and shops reopening for the occasion.
Festivities reach a fever pitch during the weekend of the Christmas Stroll—this year, Dec. 6 through 8, marks the 40th annual event—when Santa arrives via Coast Guard vessel and the annual Festival of Trees kicks off. Picturesque, cobblestone Main Street closes to traffic and you’re free to explore the holiday market and performances, hot cider in hand to combat 40-degree temperatures, as you’re transported back to the 19th century. To take care of your 21st-century travel needs, our Forbes Travel Guide editors have rounded up the best things to do, places to eat and hotels to call home during what locals simply call “Stroll.”
Cheer the VIP arrival: Be at Straight Wharf at noon on Dec. 7 to witness the town crier ringing in the Stroll and meeting Santa at the dock. Claus will step off his Coast Guard boat and into a horse-drawn carriage—heralded by trumpeters this year—before making his way to Nantucket Island Resorts’ Jared Coffin House. There, he’ll spend two hours visiting with children while live music and a Victorian costume contest go on around him. The entire Stroll embraces the Victorian theme this year; downtown, 160 seven-foot-tall trees will be decorated with antique flair, and local artist Deb Sosebee and designer Donna Elle (whose work includes the interiors of Jared Coffin House and The White Elephant) will festoon the legendary 20-foot Talking Tree atop Main Street with homemade period ornaments.
See the Festival of Trees: For more impressive greenery, visit the excellent Nantucket Whaling Museum and its annual Festival of Trees. You’ll find about 80 trees decorated by local groups—look for crafty nods to island landmarks such as Brant Point Lighthouse. Following a preview party on Dec. 5, the exhibit is open Fridays through Sundays from Dec. 6 to 29, plus on Dec. 30 and Dec. 31. Both the Whaling Museum and the Festival of Trees are open extended hours on Dec. 6, so you can ogle until 8 p.m. should the spirit strike you.
Shop the island: First introduced during the 2011 Stroll, a European-style marketplace will return at the corner of Easy and Main streets (in front of the new, only-on-Nantucket shingled Stop & Shop). From 10 a.m. to 3 p.m. on Dec. 7, find local crafts—from paintings to linens—food and hot drinks here. Brick-and-mortar boutiques all over downtown will beckon you with colorful Stroll signs, too; stop into the luxe Vanessa Noel shoe store inside the designer’s Vanessa Noel Hotel to shop its big sale—besides exquisite heels, the boutique stocks Noel’s 100-percent cashmere scarves and, for Stroll, marinara sauce canned by her Café V. (Café V will also host chef’s-table dinners inside the boutique on Friday and Saturday nights.) Even merchants from out of town are getting into the Stroll spirit. Dallas’ Commonwealth Couture vintage store will have a pop-up shop inside The Nantucket Hotel on Easton Street from Dec. 6 through 8, 9 a.m. to 4 p.m. Unique pieces begin at $25 but higher-end items include Oscar de la Renta ball gowns and men’s Scottish tweed hacking jackets. If you haven’t been in The Nantucket since its 2012 reopening after a major renovation, you’ll be taken with its clean new twist on classic Nantucket style, complete with modern lanterns, whitewashed Adirondack rocking chairs and, during Stroll, live piano music.
Cru Oyster Bar: Perched on the edge of Straight Wharf since summer 2012, Cru is about as close as you can get to the water in Nantucket without being on a boat. The oyster bar’s food and décor play off its enviable location; enjoy local seafood in dishes such as hand-cut tagliatelle with Nantucket bay scallops while seated on a blue-and-yellow banquette that evokes a whimsical yet super-sleek nautical theme. The restaurant is emerging from its off-season to serve Stroll-goers from Dec. 5 through 8, when executive chef Erin Zircher—who previously spent time in kitchens from Los Angeles’ Forbes Travel Guide Recommended Lucques to Chicago’s Forbes Travel Guide Four-Star Everest—will be preparing brunch Friday through Sunday, dinner on Friday and Saturday, and a special wine dinner with Pride Mountain Vineyards on Thursday.
Brant Point Grill: The White Elephant’s decked-out dockside restaurant is celebrating Stroll Weekend with four-course winter menus from chef Fred Bisaillon on Friday and Saturday night. Warm up in the cozy bar area between 8 and 10:30 p.m. to hear the Bob Lehman Trio play their last gigs of the season while you nurse a local Whale’s Tale Pale Ale from Cisco Brewers. On Sunday, Brant Point Grill will serve its famous brunch (start with a lobster Bloody Mary) from 10 a.m. to 3 p.m., followed by a half-price à la carte dinner between 5:30 and 10 p.m. Make reservations early for any of these meals.
Where to Stay
The White Elephant: This Nantucket Island Resorts charmer has an in-town location, gorgeous grounds and stellar amenities (think spa, yachts and lawn cocktails) to best any seaside resort. It only becomes more inviting during Stroll Weekend. Take a break from the Main Street action in the hotel’s light-filled library, where complimentary port and cheese are served every afternoon between 4 and 5 p.m. Sink into the elephant-print couch and break out a board game if you feel like staying a while. A bonus to booking a room at The White Elephant? Easy access to Brant Point Grill.
Jared Coffin House: As the host of Dec. 7’s Santa Claus meet-and-greet, this historic hotel on Broad Street puts you in the nexus of Stroll action. The antique aesthetic of the 42 recently updated guest rooms recalls the building’s 1845 debut, but all rooms are outfitted with flat-screen HDTVs and complimentary Wi-Fi. Like The White Elephant a half-mile away, Jared Coffin House hosts morning pastries and afternoon treats in its beautiful library. Should you be as charmed as we were, know this other factor that differentiates the inn from other Nantucket hotels: You can return any time because it remains open year-round.
Photos Courtesy of Nantucket Island Resorts, Nantucket Chamber Of Commerce-Michael Galvin and Cru