Nantucket’s Annual Christmas Stroll 2024 will kick-off starting Friday, December 6, 2024. The majority of festivities will be held on Saturday the 7th, and the hectic weekend will wrap-up with final events on Sunday, December 8. Now in its 50th year, Stroll is a community-oriented event sponsored by the Nantucket Island Chamber of Commerce. With a focus on shopping locally and celebrating the holiday season, there are plenty of events to spread cheer and good tidings throughout the weekend.

Nantucket Historical Association’s Festival of Trees

The premiere event of Stroll is the Nantucket Historical Association’s Festival of Trees at the Whaling Museum. On display for the whole month of December, these inspired works of art fill the entire museum. Each tree is unique and styled by the creative minds of over 50 local businesses, non-profits, and individuals.

On Display from December 6-31, 2024

Mon–Sat, 10 am–4 pm, (Closed Christmas Day)

FREE for NHA members and Island Residents

Preview Party – SOLD OUT! Thursday, December 5, 2024 from 6–8 pm, at the Whaling Museum

Public Open House at 2 White Elephant Way

Stroll on over to White Elephant Way this Friday of Stroll Weekend!

Friday, December 6th

1:00 PM – 3:00 PM

Nantucket Chamber of Commerce Hosted Events

When you arrive on island, please visit the Nantucket Chamber of Commerce at Zero Main Street, second floor, for a copy of the 2024 Official Stroll Program, or click here for the ’24 program. A merchandise and information table will also be set up at their table in the Christmas Stroll Marketplace on Stroll Saturday from 10:00 am – 3:00 pm.

SHOP SANTA’S VILLAGE: 10:00AM-3:00PM Meander through our wondrous Christmas Stroll Marketplace and celebrate the enchantment of the season.  Indulge in the aromas of delectable food and beverages as you chat with friends and survey a variety of handcrafted gifts and merchandise sold by Chamber members and non-profit organizations. Foot of Main Street.

10:00AM-3:00PM “PEOPLE’S CHOICE AWARD” STOREFRONT & TREE DECORATING CONTEST. Stroll through Town to admire the gaily decorated trees and storefronts. Place your vote for your favorite in our annual “People’s Choice Award.” Stop by the Chamber Information Table at the Shop Santa’s Village marketplace for information on trees & stores in the decorating contest!

10:00AM-5:00PM MAIN STREET STAGE ENTERTAINMENT: Stop by the stage to enjoy eclectic performances by Theatre Workshop of Nantucket, The Boys and Girls Club, The Accidentals & Naturals Nantucket High School Choir, and Victorian Carolers!  

11:50AM TOWN CRIER RINGS IN CHRISTMAS STROLL! Gather at the Main Street stage to help our inimitable Town Crier ring in our 50th Stroll!

12:00PM-2:30PM SANTA CLAUS COMES TO TOWN! Watch Santa’s arrival and join his parade as it travels up Main Street to the Pacific National Bank. Santa will be traveling in a vintage fire truck this year!

1:30PM-2:30PM TALKING TREE

2:30PM-3:00PM UGLY SWEATER CONTEST: Join us at the top of Main Street with honorary judge, Santa Claus! You know you have one, so why not get a prize for wearing it? Sign up from 10:30am to 2:30pm at the Chamber’s merchandise table at the Shop Santa’s Village marketplace. Get ready to strut your stuff!

4:30PM-5:00PM COMMUNITY CAROLING ON MAIN STREET: Join our world-renowned Victorian Carolers for a very special sing-along on the steps of Pacific National Bank on Main Street to close another amazing Christmas Stroll Saturday.

Deck the Wharf Bash at Straight Wharf Fish for Maria Mitchell Assoc.

Jingle + Mingle with the MMA as we celebrate Stroll’s 50th Anniversary with a night destined to sparkle and shine!

Date: Saturday, December 7
Time: 7 – 10pm
Location: Straight Wharf Fish, 4 Harbor Square. ️Tickets

Indulge in an evening filled with luscious bites and bubbly, featuring champagne, caviar, burgers, and more! Your ticket includes the exquisite culinary creations of chefs, Gabriel and Kevin, of Straight Wharf Fish, the luxurious flavors of Calvisius Caviar, and endless champagne and more!

And that’s not all! Get ready for: 

✨ Stargazing on the Deck
A Festive Photobooth
Cosmic Caroling
Exciting Prizes in Our Reindeer Games
Special Visits from ‘Sconset Santa, Gigi the Holiday Spirit Fairy, and Zoltar the Fortune Teller

Yuletide Fair | A Nantucket Lighthouse School Fundraiser

Nantucket Lighthouse School’s Yuletide Fair has ushered in the holiday season featuring unique handcrafted holiday items, heirloom quality gifts, a holiday Bake Shop, and holiday craft activities for children and much more. The Yuletide Fair is a cherished community event on display from 10am to 2pm.

White Elephant Ballroom, 19 North Water Street

Dreamland Stroll Party Featuring The Hess Twins

The fourth annual Dreamland Stroll Party will be held on Friday, December 6th from 7-10pm. The well-known DJ duo 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. They’ll have a Step-and-Repeat for photos, mirror photo booth, cash bar and lite bites. The Dance Party will take place in the Studio Theater with awesome lighting and decorations. 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.

Calista West Shopping Experiences

Climb the Tower of the First Congregational Church

Frog and Toad, The Musical at The Dreamland

The jazzy, upbeat score of A Year with Frog and Toad bubbles with melody and wit, making it an inventive, exuberant and enchanting musical for the whole family. Tickets for the live theatre production are available on 12/7, 12/8, 12/12, 12/13, 12/14, and 12/15.

Holiday Classics Featuring Amanda Mena 

Don’t miss this one-night-only celebration of holiday standards with Amanda Mena (Winner of The Voice, finalist on America’s Got Talent and American Idol) and her Berklee band at The Dreamland on Saturday, December 7th at 6pm in the Main Theater. This 90 minute concert will be complimented by cash bar receptions before AND after the performance in The Dreamland’s beautiful Harborview Room and Deck. Link to buy tickets.

Nantucket Lobster Trap with the Mighty Pines

Jolly Jam, Skate With Santa

3:00PM – 6:00PM, Sunday, December 8

Join the Nantucket Ice Community Rink for live music, kid’s activities, food trucks, cookies & hot cocoa! Tickets

St. Paul’s Church Concert & Christmas Market

The St. Paul’s Christmas Market will be held Saturday, December 7, 9:30 AM to 3 PM. Sit down lunch will be served from 11:30 AM to 2 PM. Great gifts, Christmas decorations, bake sale, fresh greens, and wreaths will be for sale.

The St. Paul’s Christmas Concert will be held Friday night, December 6, from 7 PM to 9 PM. Enjoy listening to holiday classics and favorite carols. Desert and bubbly will be served in the Sanctuary. Tickets are $25, cash or credit card at the door.

Book Signings at Mitchell’s

10am – 11am — Leslie Linsley, author of Christmas on Nantucket

1pm – 2pm— Debi Lilly, author of Summer Style

2pm – 3pm— Nancy Thayer, author of Let it Snow and The Summer We Started Over

3pm – 4pm— Nathaniel Philbrick, author of In the Heart of the Sea and Travels with George

4:30pm – 5:30pm— Elin Hilderbrand, author of Swan Song and The Winter Street Series

Sustainable Farmers Market at Nantucket Yacht Club

Theatre Workshop of Nantucket – Elin Hilderbrand’s Winter Street

Following a sold out run last season, this encore presentation of Elin Hilderbrand’s Winter Street comes as the New York Times Best Selling Author releases, Swan Song, her final book with the far way island of Nantucket as its backdrop and as NETFLIX premieres a star studded television event of Hilderbrand’s novel The Perfect Couple. Theatre Workshop of Nantucket takes part in celebrating Hilderbrand and just in time for the Holiday Season, as the iconic Quinn Family take the stage for a second time in Justin Cerne’s adaption of the Winter Street Series. TWN is the only place where you can see the Quinns come to life. Tickets.

Nantucket Short Film Festival

Sun, Dec 4:00 PM in the Main Theatre. Link.

Nutcracker

Get Tickets. Dec 08,2024 2:00 PM and 4:00 PM

NCMC Jazz Band Concert