Nantucket Current's Christmas Stroll Guide

The 51st Christmas Stroll will take place this weekend, and below is a list of all the events taking place on island. This year’s theme, “Shine On, Nantucket,” celebrates the resilience, unity, and spirit that make the island community truly glow, especially during the holiday season, according to the event organizer, the Nantucket Chamber of Commerce. If any events are not included in this guide, please email David Creed at davidcreed@n-magazine.com and we will add your stroll-related event to the guide.

Friday, December 5th

Sustainable Nantucket Holiday Farmers & Artisans Market

Kick off the holiday season by shopping local. Head to the Nantucket Yacht Club for a festive market filled with handcrafted gifts, seasonal treats, and the warm spirit of community. Browse a curated selection of artisans offering jewelry, pottery, textiles, candles, woodwork, and more—each piece made with care and creativity. Enjoy live music, cozy drinks, and a joyful atmosphere that celebrates the best of local craftsmanship. This will be open from 9 a.m. to 4 p.m.

ACK 4170 Stroll Pop-Up Shop

From 10 a.m. to 5 p.m. at the Dreamland Theatre, ACK 4170 will be featuring their Nantucket Christmas Stroll Candles, Stroll Merch: Totes, Tumblers, Ornaments. Holiday Cards too. Stop by and say hello, or shop online here. Weather Permitting, this will take place outside - behind the Dreamland - facing the Easy Street Boat Basin. Inclement Weather, inside the Dreamland Theatre.

Cisco Brewers Stroll Hours

Cisco Brewers will be open all Stroll Weekend. Friday from 12-7 p.m. with Jeff Tuohy performing live beginning at 4 p.m. Saturday from 11 a.m. to 7 p.m. Ian Biggs will perform form 12-4 p.m. while Jeff Tuohy will perform from 4-7 p.m. Sunday from 12 p.m. to 6 p.m. with Jeff Tuohy performing at 12 p.m.

Christmas Stroll Lunch At The Nantucket Hotel

Celebrate the magic of Nantucket’s Christmas Stroll weekend with a festive dining experience at The Nantucket Hotel. They're bringing the holiday spirit to life with sparkling décor, seasonal flavors, live entertainment, and warm island hospitality. Guests can enjoy elegant prix fixe lunch menus in our signature dining spaces at the Breeze Restaurant, in addition to a special dessert bar. From 11:30 a.m. to 3 p.m. Reserve your spot here. You can view their full calendar for Stroll Weekend here.

Epernay Wine & Spirits: Stroll Tastings! Bubbles Part 1

Come Stroll with Epernay Wine & Spirits from 1-3 p.m. They will be hosting a sparkling wine and champagne tasting featuring Roederer Estate and more.

Christmas Stroll Dessert Bar At The Nantucket Hotel

From 1:30-10 p.m., indulge in something truly special this weekend. The Nantucket Hotel's Breezeway will transform into a decadent Dessert Station featuring creations by James Beard–nominated Pastry Chef Sofia Tejeda, visiting from our sister resort, the Winnetu Oceanside Resort on Martha’s Vineyard. Treat yourself to her signature confections—each one as artful as it is irresistible.

Holiday House Tour - Friends Of Nantucket Public Schools

Join Friends of Nantucket Public Schools' for their Holiday House Tour, a beloved Stroll Weekend tradition. Step inside some of Nantucket's most beautiful homes and historic churches, each decorated in festive holiday style. Your ticket covers both days. Your ticket includes more than just a tour: with each purchase, you'll also receive admission to the Nantucket Historical Association's Festival of Trees at the Whaling Museum and the opportunity to enjoy a tower climb at the First Congregational Church, offering stunning views over town. The first 300 tickets sold will also receive a Holiday House Tour tote. All proceeds directly support Nantucket Public Schools, funding classroom resources, student programs, and educational initiatives. Celebrate the season, explore Nantucket's holiday charm and give back to the community. Purchase tickets here. From 4-7 p.m.

AAN Presents Holiday Works — Final Exhibition of 2025

The Artists Association of Nantucket (AAN) announced the opening of Holiday Works, its final exhibition of the 2025 season. This festive showcase celebrates small-scale artworks and an array of handcrafted gifts created by AAN’s talented member artists -perfect for the holiday shopper seeking something meaningful, unique, and authentically Nantucket. Holiday Works opened on November 21. The season’s highlight, the annual Cool Yule Exhibition Reception, will be held on Friday, December 5, from 4-6 p.m., offering guests an evening of artwork, community, and holiday cheer. Theexhibition will remain on view through December 24. The exhibition will include new works by many of AAN’s most popular artists. Shoppers will find a wide selection of special holiday gift items, including mini paintings, ceramic ornaments, ceramic birds, and other delightful surprises created exclusively for the season.

The Nantucket Hotel Stroll Dinner At Breeze With Live Entertainment

Celebrate the magic of Nantucket’s Christmas Stroll weekend with a festive dining experience at The Nantucket Hotel. They’re bringing the holiday spirit to life with sparkling décor, seasonal flavors, live entertainment, and warm island hospitality. Guests can enjoy an elegant prix fixe dinner menu in our signature dining spaces at the Breeze Restaurant. From 5-10 p.m.

Christmas Carolers At The Nantucket Hotel, Sailor’s Valentine Front Deck Carolers With Cocktails, Flatbreads And Lite Bites

Christmas Carolers at the Nantucket Hotel, Sailor’s Valentine front porch featuring carolers with cocktails, flatbreads, and lite bites. This will take place from 5-6 p.m.

Live Music At The Nantucket Hotel, Sailor’s Valentine Front Deck Live Music, Saxophone With Damien

From 6-8 p.m. at the Nantucket Hotel, Sailor’s Valentine front deck live music, Saxophone with Damien.

Deck The Wharf Bash Stroll Weekend With The MMA

The Maria Mitchell Association is thrilled to celebrate stroll with you at their second annual Deck The Wharf Bash from 7-10 p.m. at 4 Harbor Square. Celebrate the magic of Nantucket’s Christmas Stroll with the MMA. Join them for an enchanting evening of holiday cheer and culinary decadence, a night destined to sparkle and shine. Delight in a festive tasting experience crafted by Chefs Gabriel and Kevin of Straight Wharf Fish, featuring caviar, gourmet bites, burgers, and more. Toast the season with champagne and seasonal cocktails as you bask in the twinkling lights and joyful spirit of Stroll. The evening is brimming with holiday delights: Stargazing on the Deck under Nantucket’s crisp winter sky; Magical moments with Roaming Magician, Magic Mark; Festive Photo Opportunities to capture the season; Cosmic Caroling to fill the air with cheer; and Holiday Prizes and a Gift Giveaway to make spirits bright. Don your festive attire, bring your holiday spirit, and join us for a night where sparkle, flavor, and Stroll festivities come together to celebrate the season on Nantucket. Only 100 tickets are available for this exclusive holiday fundraiser supporting their year-round programs. Individual tickets are $650 ($400 is tax-deductible).

5th Annual Nantucket Dreamland Stroll Party

Join the Dreamland for their fifth annual Stroll Party on the second floor of Dreamland from 7-10 m. The Hess Twins will be performing your favorite top 40, classic, and holiday hits to dance the night away to. Dress in your finest Stroll garb and they’ll have a contest for the best dressed, with the winner taking home four tickets to their Daffodil weekend party. We’ll have a step-and-repeat for photos along with a cash bar and catered lite bites. The dance party will take place in the studio theater with festive lighting and decorations to match the holiday season. Food and areas to relax will be available in the Harborview Gallery and deck. This event sells out every year, so don’t delay in getting your tickets. General Public: $43 ($40 + $3 Service Fee). Dreamland Members: $35 (No Service Fee) Age Requirement: 18 & Above, 21+ wristband

St. Paul's Christmas Concert

It's beginning to sound a lot like a Christmas Concert. Join St. Paul's Episcopal Church at 20 Fair Street for holiday classics, favorite carols featuring vocal soloists, instrumentalists, and a sing-a-long. Tickets are $25 per person - cash, credit card or Venmo at the door. The concert will be followed by dessert and a bubbly reception. This concert will take place from 7-9 p.m. at St. Paul's Church at 20 Fair Street. Doors open at 6:30 p.m. There will also be a silent auction after the concert.

Live Music & Dinner At The Lobster Trap

The Lobster Trap (23 Washington Street) will have the live band "The Mighty Pines" from St. Louis playing on Friday, December 5th and Saturday, December 6th from 8-10 p.m. On Friday, they will serve dinner beginning at 5 p.m. followed by the live band. On Saturday, they will serve lunch beginning at 11 a.m. and then dinner followed by the live band. On Sunday, the Lobster Trap will be open for lunch

Nantucket Hotel Live Entertainment

From 8-10 p.m., there will be live entertainment with DJ Billy Voss at the Nantucket Hotel's Club Lounge.

Live Music & Karaoke At The Rose & Crown

From 8-11:55 p.m., go and celebrate Stroll at the Rose & Crown. Live music with Sean Lee is from 8-10 p.m. Karaoke will take place from 10 p.m. to close. On Sunday, there will be a closing party all day long. All tips on Sunday will be donated to Marla Lamb & Jamaican relief.

Beach Nights Live Music At The Chicken Box

There will be live music at the Chicken Box beginning at 10 p.m. and it will be performed by Beach Nights on Friday and Saturday.

Live Music At The Gaslight

There will be live music Friday and Saturday at the Gaslight, performed by Supertaste. It will begin at 10 p.m.

Saturday, December 6th:

St. Paul's Christmas Market

From 9:30 a.m. to 3 p.m., The Christmas Market at St. Paul's Church will be open. Great Shopping and Seated Lunch. Christmas Decorations & Seasonal Decor; Carefully Curated Gifts; Nantucket Themed Items; Jewelry, Holiday Bake Sale; and Silent Auction & Fresh Wreaths. For Lunch, from 11:30 a.m. to 2:30 p.m., sit down, warm up and enjoy Chowder, Quiche, Chili, Vegetarian Soup, Hot Dogs, and Salad.

51st Nantucket Christmas Stroll: Marketplace

The Nantucket Island Chamber of Commerce invites you to their 51st Nantucket Christmas Stroll: Marketplace from 10 a.m. to 3 p.m. in the Stop & Shop Lot, 9 Salem Street. The most anticipated market of the year is just around the corner. Shop the best Nantucket has to offer from a versatile group of Craftspeople, Artist and Artisans, Jewelers, Photographers and Retailers to name a few. The marketplace also hosts a number of notable Nantucket based Non-profits and features an entire row dedicated to culinary creations from local Food Truck vendors and Restaurateurs. Every participant is a proud member of Nantucket Island Chamber of Commerce. There is no entry fee for patrons, just come ready to shop 'til you drop.

Book Signing With Alison Barone & Annabelle Meszynski

From 10-11 a.m., the author and illustrator of Nantucket Nelly and the Christmas Stroll will be at Mitchell's Book Corner, 54 Main Street for a book signing.

Yuletide Fair

From 10 a.m. to 4 p.m., join the Lighthouse School in kicking off the season at their Yuletide Fair, a winter marketplace brimming with handcrafted treasures, coastal-inspired gifts and homemade baked goods. With Stroll as the perfect backdrop, this mainstay event brings together islanders and visitors alike in support of the Nantucket Lighthouse School. This will take place in the White Elephant Ballroom at 19 North Water Street.

ACK 4170 Stroll Marketplace Pop-Up

Along with Nantucket Island Chamber of Commerce Members, ACK 4170 will be participating in the Stroll Marketplace. They will be featuring their Nantucket Christmas Stroll Candles, Stroll Merch: Totes, Tumblers, Ornaments, Holiday Cards too, Stop by and say hello.

Holiday House Tour - Friends Of Nantucket Public Schools

Join Friends of Nantucket Public Schools' for their Holiday House Tour, a beloved Stroll Weekend tradition. Step inside some of Nantucket's most beautiful homes and historic churches, each decorated in festive holiday style. Your ticket covers both days. Your ticket includes more than just a tour: with each purchase, you'll also receive admission to the Nantucket Historical Association's Festival of Trees at the Whaling Museum and the opportunity to enjoy a tower climb at the First Congregational Church, offering stunning views over town. The first 300 tickets sold will also receive a Holiday House Tour tote. All proceeds directly support Nantucket Public Schools, funding classroom resources, student programs, and educational initiatives. Celebrate the season, explore Nantucket's holiday charm and give back to the community. Purchase tickets here. From 10 a.m. to 1 p.m. Tickets are good for both Friday's and Saturday's tours.

NCMC Music Performances

The NCMC Youth Choir on Main Street beginning at 11 a.m. Look for their Youth Choir spreading holiday cheer right on Main Street during Stroll festivities. Come enjoy seasonal favorites performed by their youngest singers.

Book Signing With Leslie Linsley

From 11 a.m. to 12 p.m., at Mitchell's Book Corner (54 Main Street), there will be a book signing with Leslie Linsley, the author of Christmas on Nantucket.

Photos With Santa + Flash Sales At The Susan Lister Locke Gallery

From 11 a.m. to 3 p.m. at the Susan Lister Locke Gallery (28 Easy Street), Santa will be at the gallery on Saturday for photos. Enjoy flash sales throughout the day when Susie rings the bell.

Prix Fixe Christmas Stroll Lunch At Breeze At The Nantucket Hotel

Celebrate the magic of Nantucket’s Christmas Stroll weekend with a festive dining experience at The Nantucket Hotel. They're bringing the holiday spirit to life with sparkling décor, seasonal flavors, live entertainment, and warm island hospitality. Guests can enjoy elegant prix fixe lunch menus in our signature dining spaces at the Breeze Restaurant, in addition to a special dessert bar. From 11:30 a.m. to 3 p.m. Reserve your spot here.

Book Signing With Pamela Kelley

From 12-1 p.m., there will be a book signing with Pamela Kelley at Mitchell's Book Corner (54 Main Street).

Book Signing With James Sulzer, Author Of All That Smolders

From 1-2 p.m., there will be a book signing with James Sulzer at Mitchell's Book Corner (54 Main Street).

Epernay Wine & Spirits: Stroll Tastings! Bubbles - Part II

From 1-3 p.m., come Stroll with Epernay Wine & Spirits. They will be hosting a Champagne tasting featuring Perrier-Jouët and more. Location is 1 North Beach Street.

Dessert Bar At Nantucket Hotel

There will be a dessert bar at the Nantucket Hotel, Breeze Lounge. Inspired desserts made and served Sofia Tejada, James Beard Nominated Pastry Chef. This will take place from 1:30-10 p.m.

Book Signing With Nancy Thayer

There will be a book signing with Nancy Thayer, author of Summer Light On Nantucket and A Very Nantucket Christmas, at Mitchell's Book Corner (54 Main Street) from 2-3 p.m.

Book Signing With Nathaniel Philbrick

From 3-4 p.m., there will be a book signing With Nathaniel Philbrick, author of In the Heart of the Sea and Travels with George, at Mitchell's Book Corner (54 Main Street).

Christmas Stroll Prix Fixe Dinner At The Nantucket Hotel

There will be a Christmas Stroll Prix Fixe Dinner at the Nantucket Hotel from 5-10 p.m. at the Breeze with live entertainment Nicole Miller & Jepthe – Piano & Vocals.

Live Music At Nantucket Hotel

From 6-8 p.m. at the Nantucket Hotel, there will be live music with saxophonist, Damien at the Nantucket Hotel, Sailor’s Valentine front porch. DJ Billy Voss will be performing from 8-10 p.m.

Cranberry Alarm Clock At Faregrounds

Head to Faregrounds/Pudley's Pub for some festive music as Cranberry Alarm Clock will be playing live beginning at 8 p.m. on Saturday, December 6th.

Beach Nights Live Music At The Chicken Box

There will be live music at the Chicken Box beginning at 10 p.m. and it will be performed by Beach Nights

Sunday, December 7th

Rose & Crown Closing Party

There will be a closing party all day long. All tips on Sunday will be donated to Marla Lamb & Jamaican relief.

Christmas Stroll Brunch At Nantucket Hotel

There will be a special Christmas Stroll brunch with live entertainment at the Nantucket Hotel, Breeze from 8 a.m. to 1 p.m.

ACK 4170 Stroll Pop-Up Shop

From 10 a.m. to 5 p.m. at the Dreamland Theatre, ACK 4170 will be featuring their Nantucket Christmas Stroll Candles, Stroll Merch: Totes, Tumblers, Ornaments. Holiday Cards too. Stop by and say hello, or shop online here. Weather Permitting, this will take place outside - behind the Dreamland - facing the Easy Street Boat Basin. Inclement Weather, inside the Dreamland Theatre.

Holiday Fun Day & Santa Visit At The Nat. Sci. Museum

From 10:30 a.m. to 2 p.m., join the Maria Mitchell Association at the Hinchman House (7 Milk Street) for a fun-filled day of festive celebration and celebrate the end of Stroll Weekend the Maria Mitchell Way. Create Your Own Holiday Ornaments from 10:30 a.m. to 12 p.m. Take home a special keepsake you’ve made yourself. Animal Meet & Greet from 10:30 a.m. to 1:30 p.m. Meet their animals up close during one-on-one encounters. Nature Story Time will be at 11:30 a.m. Don’t Let the Pigeon Drive the Sleigh by Mo Willems. Visit from Santa from 12 m. to 2 p.m. Bring your family and friends and help them wrap up the season with creativity, curiosity, and holiday cheer. Admission is free to all. No registration necessary.

John Shea Reads "A Child's Christmas in Wales" At St. Paul's Church

Emmy Award winning actor and TWN Artistic Director Emeritus John Shea will present a dramatic reading of two classic Christmas short stories: Dylan Thomas' A Child's Christmas In Wales and Truman Capote's A Christmas Memory. This will take place at noon at St. Paul's Episcopal Church at 16 Fair Street. Admission is free.

NCMC Community Chorus Holiday Concert

On Sunday, December 7th, ring in the season with a beautiful afternoon of choral music performed by the NCMC Community Chorus. This concert will talk place at St. Paul's Church (20 Fair Street).