Christmas Stroll on Nantucket is pure magic. From children’s activities in the mornings to festive nightlife and holiday dining in the evenings, the island truly comes alive. Whether you’re here for the shopping, the history, the music, or simply the tradition, we’ve highlighted the weekend’s events below to help you enjoy every moment.
Below is your full lineup of events for Stroll Weekend 2025:
🎄 Friday, December 5, 2025
9:00AM - 4:00PM Holiday Farmers & Artisans Market
Sustainable Nantucket | Nantucket Yacht Club, 1 South Beach Street
Kick off the weekend by shopping local; seasonal treats, handcrafted gifts, and festive cheer abound.
9:50AM - 11:00AM Fabulous Mansions of Cliff Rd & Brant Point
Nantucket Walking Tours | Meet at Federal & India
Enjoy a one-hour guided tour of Nantucket’s historic and iconic summer homes. Admission fee.
10:00AM - 5:00PM ACK 4170 Pop-Up Shop
Dreamland Theatre, 17 South Water Street
Browse Stroll candles, totes, tumblers, ornaments, and holiday cards.
11:30AM - 3:00PM Christmas Stroll Lunch
Breeze at The Nantucket Hotel, 77 Easton Street
A festive dining experience in the heart of the island.
1:30PM - 10:00PM Dessert Bar
Breeze at The Nantucket Hotel
A decadent dessert station crafted by James Beard–nominated pastry chef Sofia Tejada.
1:50PM - 3:20PM Historic Downtown Walking Tour
Nantucket Walking Tours | Meet at Federal & India
An 80-minute tour exploring why Nantucket is known as “the most important small town in American history.” Admission fee.
3:00PM - 3:45PM Nature Story Time
Maria Mitchell Association | Hinchman House, 7 Milk Street
Perfect for young explorers, a story time with animal ambassadors, and a hands-on activity. Admission fee.
4:00PM - 7:00PM Holiday House Tour
Friends of Nantucket Public Schools | 2 Centre Street
Step inside beautifully decorated island homes. Admission fee
5:00PM - 6:00 PM Stroll Dinner with Live Entertainment
Breeze at The Nantucket Hotel
A festive dining experience in the heart of the island.
6:00PM - 8:00PM Live Music on the Front Porch
The Nantucket Hotel | Sailor’s Valentine Porch
Saxophonist Damien performs live.
7:00PM - 9:00 PM Christmas Concert
St. Paul’s Episcopal Church, 20 Fair Street
Holiday classics, carols, and desserts afterward. Admission fee.
7:00PM - 10:00PM Dreamland Stroll Party
Dreamland | 17 South Water Street
Dance the night away with DJ duo The Hess Twins. Admission fee.
7:00PM - 10:00 PM Deck the Wharf Bash
Maria Mitchell Association | Straight Wharf Fish
Champagne, seasonal cocktails, caviar, burgers, and festive bites.
8:00PM - 10:00PM DJ Billy Voss
The Nantucket Hotel | Club Lounge
Dance the night away with DJ Billy Voss in the Club Lounge
🎁 Saturday, December 6, 2025
9:00AM - 4:00PM Holiday Farmers & Artisans Market
Sustainable Nantucket | Nantucket Yacht Club, 1 South Beach Street
Continue to enjoy the weekend by shopping local; seasonal treats, handcrafted gifts, and festive cheer abound.
9:30AM - 3:00PM Christmas Market
St. Paul’s Episcopal Church, 20 Fair Street
Browse jewelry, baked goods, chowder, chili, and Nantucket-themed gifts.
10:00AM - 10:45AM Morning Exercise Walk with Historic Commentary
Meet at Federal & India
A 1.5-mile informative walk about the history of whaling, America's oldest windmill and much more. Admission fee.
10:00AM - 3:00PM 51st Christmas Stroll Marketplace
Stop & Shop Downtown Lot | 9 Salem Street
Artists, jewelers, photographers, and more.
10:00AM - 1:00PM Holiday House Tour
Friends of Nantucket Public School | 2 Centre Street
Step inside some of the island's most beautiful homes and churches that will be decorated for the festivities. Admission fee
10:00AM - 4:00PM Nantucket Lighthouse School Yuletide Fair
White Elephant Ballroom
Enjoy a winter marketplace with handcrafted treasures, island fights and much more to support Nantucket Lighthouse School.
Book Signings at Mitchell’s Book Corner (54 Main Street)
- 10:00–11:00 AM : Alison Barone & Annabelle Meszynski, Author and illustrator of Nantucket Nelly and the Christmas Stroll
- 11:00–12:00 PM : Leslie Linsley, Author of Christmas on Nantucket
- 12:00–1:00 PM : Pamela Kelley, Author of Christmas at the Nantucket Restaurant
- 1:00–2:00 PM : James Sulzer, Author of All that Smolders
- 2:00–3:00 PM : Nancy Thayer, Author of Summer Light on Nantucket and A Very Nantucket Christmas
- 3:00–4:00 PM : Nathaniel Philbrick, Author of In the Heart of the Sea and Travels with George
- 4:30–5:30 PM :Elin Hilderbrand, Author of The Academy and The Winter Street Series
11:30AM - 3:00PM Prix Fixe Lunch
Breeze at The Nantucket Hotel
Enjoy a festive dining experience at The Nantucket Hotel, prix fixe dinner menu with signature dining spaces.
1:30PM - 10:00PM Dessert Bar
Breeze at The Nantucket Hotel
The Breezeway will transform into a decadent dessert station featuring creations by James Beard-nominated pastry chef, Sofia Tejada.
1:50PM - 3:20PM Historic Downtown Walking Tour
An 80-minute tour exploring why Nantucket is known as “the most important small town in American history.” Admission fee.
4:00PM - 7:00PM Jon Stetson, America’s Master MentalistThe Nantucket Hotel | Club Lounge
5:00PM – 6:30PM Nantucket Ghost Walk (Town Route)
Meet at Federal & India
A spooky 80-minute walk to five haunted locations. Admission fee.
5:00PM – 6:00PM Stroll Dinner with Live Entertainment
Breeze at The Nantucket Hotel | 77 Easton Street
Enjoy a festive dining experience at The Nantucket Hotel, prix fixe dinner menu with signature dining spaces.
5:30PM – 6:30PM Carolers on the Front Porch
The Nantucket Hotel | Sailor’s Valentine Porch, 77 Easton Street
Carolers with cocktails and apps!
6:00PM - 8:00PM Live Music on the Front Porch
The Nantucket Hotel | Sailor’s Valentine Porch
8:00PM - 10:00PM DJ Billy Voss
The Nantucket Hotel | Club Lounge
Dance the night away with DJ Billy Voss in the Club Lounge
⭐ Sunday, December 7, 2025
11:30AM - 3:00PM Christmas Stroll Lunch
Breeze at The Nantucket Hotel, 77 Easton Street
A festive dining experience in the heart of the island.
10:00AM - 11:00AM Fabulous Mansions Tour
Nantucket Walking Tours | Meet at Federal & India
Enjoy a one-hour guided tour of Nantucket’s historic and iconic summer homes. Admission fee.
10:00AM - 2:00PM Stroll Sunday Brunch
Or, The Whale | 38 Main Street
10:00AM - 5:00PM ACK 4170 Pop-Up Shop
ACK 4170, Dreamland Theatre, 17 South Water Street
Featuring Nantucket Christmas Stroll Candles, Stroll Merch: Totes, Tumblers, Ornaments and Holiday Cards!
1:00PM - 1:45PM Ornament Making
Maria Mitchell Association, The Hinchman House Natural Science Museum, 7 Milk Street
Join MMA for nature-inspired crafting, young makers and their families will explore the wonders of the natural world through hands-on projects. Admission Fee
1:50PM - 3:20PM Historic Downtown Walking Tour
Nantucket Walking Tours | Meet at Federal & India
An 80-minute tour exploring why Nantucket is known as “the most important small town in American history.” Admission fee.
4:50PM - 6:30PM Nantucket Ghost Walk (Town Route)
Meet at Federal & India
A spooky 80-minute walk to five haunted locations. Admission fee.
As the lights twinkle down Main Street and the island comes together in celebration, Christmas Stroll reminds us why Nantucket is such a special place to call home or to dream of calling home someday.
If Stroll Weekend has you imagining your own Nantucket getaway, a seasonal rental, or even a home of your own, Lee Real Estate is here to help. With local market knowledge and decades of experience, our team is always happy to guide you.