From December 5 through 7, the cobblestoned streets of Nantucket are transformed into something of a Dickensian tableau during the island’s 51st Annual Christmas Stroll. Conceived in 1973 by a collective of savvy island merchants, the weekend event was originally founded to combat the pre-winter exodus, enticing islanders and mainlanders alike to stay, visit, and most importantly, shop locally. Today, this tradition draws thousands to support Nantucket’s cherished small businesses while enjoying the incomparable holiday ambiance of the historic district.

This year’s Stroll is chock-full of festivities—from shopping events and Santa sightings to live music and beyond—outlined below. Happy Strolling!

Friday, December 5

Ease into the weekend with local markets, festive tours, and the first toast of the season.

9:00 AM: Wreath Making Workshop
Bartlett’s Farm (33 Bartlett Farm Road)
*Ed. Note: Other sessions start at 11:00 AM and 1:00 PM.

9:00 AM – 4:00 PM: Holiday Farmers & Artisans Market
Nantucket Yacht Club (1 South Beach Street)
*Ed. Note: Skip the generic gifts and head here first. It’s the perfect spot to grab local pottery, hand-knit goods, and island-made jewelry before the Saturday crowds descend.

10:00 AM – 4:00 PM: Whaling Museum Festival of Trees
Whaling Museum (13 Broad Street)
*Ed. Note: Opening day; runs through December. Dozens of locally designed trees set against the backdrop of the historic museum. It’s arguably the most Instagrammable spot of the weekend.

1:00 PM – 3:00 PM: Bubbles & Stroll Tasting
Épernay Wine & Spirits (1 N Beach Street)

4:00 PM – 7:00 PM: Holiday House Tour
Various Locations (Begins at 2 Centre Street)
*Ed. Note: A chance to step inside some of the island’s most stunning historic homes and churches, all dressed up for the holidays. Proceeds benefit Friends of Nantucket Public Schools.

5:00 PM - 6:30 PM: The Nantucket Ghost Walk
Various Locations (Begins at the corner of India and Federal Streets)

5:00 PM - 8:00 PM: Live Music on the Front Porch
The Nantucket Hotel (77 Easton Street)
*Ed. Note: Carolers, cocktails, and more.

7:00 PM - 8:00 PM: Christmas Concert
St. Paul’s Episcopal Church (20 Fair Street)

7:00 PM - 10:00 PM: 5th Annual Nantucket Dreamland Stroll Party
Dreamland Nantucket (17 S Water Street)
*Ed Note: A ticketed event with a DJ performance by the Hess Twins.

7:00 PM - 10:00 PM: Deck the Wharf Bash
Maria Mitchell Association at Straight Wharf Fish (4 Harbor Square)

Saturday, December 6

The big day. Wear your festive best (yes, that means ugly sweaters, reindeer antlers, flashing bulb necklaces—Stroll knows no style shame!).

9:00 AM – 4:00 PM: Holiday Farmers & Artisans Market
Nantucket Yacht Club (1 South Beach Street)

9:30 AM: Christmas Stroll Auction
Rafael Osona (21 Washington Street)

9:30 AM – 3:00 PM: Christmas Market
St. Paul’s Episcopal Church (20 Fair Street)

10:00 AM – 2:00 PM: St. Mary’s Cookout
St. Mary’s Church (3 Federal Street)

10:00 AM – 3:00 PM: 51st Annual Christmas Stroll Marketplace
Nantucket Island Chamber of Commerce at the Stop & Shop Downtown Lot (9 Salem Street)
*Ed. Note: This is what Stroll is all about. Support local businesses!

10:00 AM - 5:30 PM: Book Signings
Mitchell’s Book Corner (54 Main Street)
*Ed. Note: 10:00 AM - 11:00 AM with Alison Barone and Annabelle Meszynski, author and illustrator (respectively) of Nantucket Nelly and the Christmas Stroll; 11:00 AM - 12:00 PM with Leslie Linsley, author of Christmas on Nantucket; 12:00 PM - 1:00 PM with Pamela Kelley, author of Christmas at the Nantucket Restaurant; 1:00 PM - 2:00 PM with James Sulzer, author of All That Smolders; 2:00 PM - 3:00 PM with Nancy Thayer, author of Summer Light on Nantucket and A Very Nantucket Christmas; 3:00 PM - 4:00 PM with Nathaniel Philbrick, author of In The Heart of the Sea and Travels with George; 4:00 PM - 5:30 PM with Elin Hilderbrand, author of The Academy and Winter Street Series

10:00 AM – 1:00 PM: Holiday House Tour
Various Locations (Begins at 2 Centre Street)

10:00 AM – 4:00 PM: Yuletide Fair
Nantucket Lighthouse School at White Elephant Ballroom (19 N Water Street)

11:00 AM – 7:00 PM: Cisco Brewers
Cisco Brewers (Bartlett Farm Rd)
*Ed. Note: Take the shuttle from downtown. Live music, raw bar, and festive crowds.

12:00 PM (Sharp!): Santa’s Arrival by Boat
Straight Wharf
*Ed. Note: The Town Crier announces 10 minutes before the event. Santa arrives via Coast Guard cutter. Avoid the crowd at the dock; instead, watch from the gazebo area or stake out a spot on Main Street early to see him parade up to the Pacific National Bank.

1:30 PM – 2:30 PM: The Talking Tree
Main Street
*Ed. Note: Pure nostalgia. The “Talking Tree” is a quirky island tradition that terrifies and delights children in equal measure.

3:00 PM – 4:30 PM: Accidentals & Naturals
Main Street
*Ed. Note: Nantucket High School’s chorus performs a selection of holiday songs.

3:30 PM – 4:00 PM: Ugly Sweater Contest
Main Street

4:15 PM – 5:00 PM: Victorian Carolers Sing-Along
Main Street

Sunday, December 7

The cherry on top of a weekend full of holiday cheer.

7:00 AM: Monument Running Group Annual Winter Run
Various Locations (Begins at Nantucket Run Centre, 36 Centre Street)

1:00 PM – 4:00 PM: Ornament Making
Maria Mitchell Association at the Hinchman House Natural Science Museum (7 Milk Street)

2:00 PM: The 12th Annual Nantucket Nutcracker
Nantucket High School Auditorium (10 Surfside Road)
*Ed. Note: Also at 5:00 PM. A shorter, family-friendly production by the Nantucket Dance Theater. A sweet way to end the weekend.

5:00 PM: A Christmas Story: The Play
Theatre Workshop of Nantucket (62 Centre Street)

And just like that, peak season is in our rearview and Thanksgiving is upon us. From the Cold Turkey Plunge to Main Street’s Annual Tree Lighting Ceremony and even restaurants open for Thanksgiving takeaway or dining in on the day, the holiday week’s events mark just the beginning of the merriment that’s to come. Your agenda for celebrating the holiday on Nantucket, below.

Wednesday, November 26

Turkey Karaoke!
The Gaslight, 3 N Union Street

Open restaurants: 45 Surfside Cafe, Bar Yoshi, Bartlett’s Farm, Billie’s, Black Eyed Susan’s, Brant Point Grill, Breeze at the Nantucket Hotel, Kitty Murtagh’s, Pip & Anchor, Pizzeria Gemelle, Proprietors, Sister Ship, Surfside Taco Stand, The Brotherhood, The Pearl, The Whale, Wicked Island Bakery

Thursday, November 27

Cold Turkey Plunge
Children’s Beach
9AM-10:30AM

Epernay Wine Tasting
Epernay Wine & Spirits, 1 N Beach Street
4PM-6PM

Open restaurants: Billie’s, Brant Point Grill, Breeze at the Nantucket Hotel, Company of the Cauldron (for takeaway), Oran Mor, Provisions, Sister Ship (1PM-6PM)

Friday, November 28

Sustainable Nantucket Holiday Farmers and Artisans Market
Cambridge Street & North Union Street
10AM-2PM

Christmas Tree Lighting and Community Caroling
Main Street
4PM

Sip, Shop, and Sea
Shipwreck & Lifesaving Museum, 158 Polpis Road
4PM-7PM

The Nantucket Ghost Walk
Main Street
7PM

Thanksgiving Eve Stargazing
Loines Observatory, 59 Milk Street Ext
7PM or 8PM

Buckle & Shake
Gaslight, 3 N Union Street

Open restaurants: 45 Surfside Cafe, B-ACK Yard BBQ, Bar Yoshi, Bartlett’s Farm, Billie’s, Black Eyed Susan’s, Brant Point Grill, Breeze at the Nantucket Hotel, Kitty Murtagh’s, Millie’s Mid-Island at the Rotary, Oran Mor, Pizzeria Gemelle, Proprietors, Provisions, Sister Ship, Surfside Taco Stand, The Brotherhood, The Corner Table, The Pearl, The Whale, Ventuno, Via Mare

Saturday, November 29

Nantucket Bird Walk
Maria Mitchell Association Research Center, 2 Vestal Street
7:45AM-10AM

Sustainable Nantucket Holiday Farmers and Artisans Market
Cambridge Street & North Union Street
10AM-2PM

Fabulous Mansions of the Cliff and Brant Point
Federal Street & India Street
10AM

Morning Exercise Walk With Historic Commentary
Federal Street & India Street
10AM

Chris Matthews Book Signing
Mitchell’s Book Corner, 54 Main Street
10:30AM-12PM

Nanpuppets
The Gaslight, 3 Union Street
2:30PM-5PM

Open restaurants: 45 Surfside Cafe, B-ACK Yard BBQ, Bar Yoshi, Bartlett’s Farm, Billie’s, Black Eyed Susan’s, Brant Point Grill, Breeze at the Nantucket Hotel, Kitty Murtagh’s, Millie’s Mid-Island at the Rotary, Oran Mor, Pip & Anchor, Pizzeria Gemelle, Proprietors, Provisions, Sister Ship, Surfside Taco Stand, The Brotherhood, The Pearl, The Whale, Ventuno, Via Mare, Wicked Island Bakery

Sunday, November 30

Open restaurants: 45 Surfside Cafe, B-ACK Yard BBQ, Bar Yoshi, Bartlett’s Farm, Black Eyed Susan’s, Brant Point Grill, Breeze at the Nantucket Hotel, Kitty Murtagh’s, Millie’s Mid-Island at the Rotary, Oran Mor, Pip & Anchor, Pizzeria Gemelle, Provisions, Surfside Taco Stand, The Brotherhood, The Whale, Ventuno, Via Mare, Wicked Island Bakery

Fifty years ago this summer, a film changed moviemaking as we know it. Behind an unassuming single-word title, Jaws not only terrified moviegoers around the globe, it also invented the summer blockbuster, forever altering how Hollywood makes and markets its biggest hits. Now, a new documentary, Jaws @ 50: The Definitive Story (premiering on National Geo…

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Stepping into The Vault Nantucket is like entering another world: a globally-influenced, gem-filled world where color is queen, better known as Katherine Jetter’s world. As the founder of the jewel box of a boutique on Centre Street and jewelry designer herself, Jetter brings a curation of couture design to the island, sharing her passion for exquisite …

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For over five decades, Nantucket Looms has stood as a Main Street mainstay, woven into the fabric of the island’s cultural identity. Known for its luxe handwoven textiles, thoughtfully curated home décor, and personalized interior design services, the beloved institution is now turning a new page—literally—with the release of its first-ever book, Nantucket Looms: A Legacy of Style (Rizzoli). This richly crafted volume offers an intimate look at the store’s origins, community impact, and the notable figures who have helped shape its enduring legacy.

The story of Nantucket Looms began in the early 1960s, when island residents Bill Euler and Andrew Oates crossed paths with Walter Beinecke, the visionary responsible for reshaping Nantucket into a world-class destination. Back then, the island was far from the picture-perfect postcard it is today. Its wharves were gritty, and its colonial charm had faded. But Beinecke’s plan to restore Nantucket’s historic beauty laid the groundwork for what would become a new era—and the birth of Nantucket Looms.

Inspired by this revival, Euler and Oates purchased The Cloth Company in 1968, an initiative founded by the Nantucket Historical Trust to create reproduction textiles for historic renovations like the Jared Coffin House. When the Trust’s projects wound down, the duo transformed the company into a retail store and weaving studio—marking the official founding of Nantucket Looms as we know it.

As the business grew, so too did its offerings. After Euler and Oates retired, the baton was passed to their successor, current co-owner and president Bess Clarke’s mother, Liz Winship, who expanded the store’s offerings to include furniture, home décor, and even personalized interior design in the 1990s. As clients increasingly sought advice on arranging their spaces, Clarke explained, it made sense to formalize it. Located on the store’s upper floor, the design studio invites customers to explore the materials and designs, offering a tactile, immersive experience.

From inception, Nantucket Looms has been deeply integrated and committed to the island’s local community. “One of the big pillars of our business has always been to employ a year-round workforce,” says Clarke. “Even when it didn’t make financial sense, [Bill and Andy] honored that commitment.” Unlike many seasonal shops, Nantucket Looms chose to keep its doors open and its payroll running through the off-season—offering health insurance and full benefits to its employees, a practice that continues to this day.

Further, Nantucket Looms supports local artists through a traditional consignment relationship. “It’s this wonderful, old-school system. Seeing them walk in with their paintings, jewelry, textiles—it’s one of the most charming parts of the business,” says Clarke. “The better our business does, the better it is for the artists. And that’s something that makes me really proud.”

The allure of Nantucket Looms hasn’t gone unnoticed. Over the years, the shop has quietly built a clientele as storied as its legacy. Its new book offers glimpses into some of these memorable relationships—from legendary interior designers like Billy Baldwin to style icons such as Jackie Kennedy Onassis and Bunny Mellon.

“We still have [Jackie Kennedy’s] handwritten letters,” Clarke says, recalling the First Lady’s endearing notes, inquiring about gifts for her son or even sweater exchanges. “She had this beautiful stationery, but she would scratch out half the letter and not even start a new letter—it was just really funny.” One such letter is currently framed in the store’s weaving studio.

“Over the years, we’ve had everyone from Lady Bird Johnson and Hillary Clinton (lots of First Ladies would come in and visit the weaving studio) to Tom Selleck (who my mom wrapped her arms around to measure for a shirt jacket and was like ‘Oh my gosh,’ for about ten years after),” says Clarke, who also recalls a visit from American actress Grace Kelly. “There’s a story about Grace Kelly coming into the shop wearing a turban, eating an ice cream cone—which, of course, was not allowed in the store. But what do you say to Grace Kelly?”

Now, with its new book—featuring writing by Linda Jane Holden (author of Rizzoli’s The Gardens of Bunny Mellon) and Mitchell Owens (editor-in-chief of The Magazine Antiques), and photography by Matt Kisiday—Nantucket Looms: A Legacy of Style invites readers into its home of history, community, and craftsmanship—with a few celebrity anecdotes along the way. “My mom was such an incredible oral historian. You’d walk into the shop, and she’d share these great stories, little tidbits about the island, about the artists. But now she’s not in the store anymore, and I didn’t want that history to be lost. I wanted to capture it, pass it on, and share the lessons we learned from Bill, Andy, Liz, and all the people who have shaped this place over the last 50+ years.”

(Photos courtesy of Nantucket Looms)

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