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2023 Nantucket Stroll


Events & Traditions

2023 nantucket stroll
@fishernantucket STROLLING! #nantucket ♬ It's Beginning to Look a Lot like Christmas – Michael Bublé

Nantucket’s Annual Christmas Stroll 2023 will be underway on December 1, 2023, with festivities planned through December 3, 2023. Now in its 49th 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.

Brant Point Holiday Wreath by Hafsa & Co

Nantucket Historical Association’s Festival of Trees

Gather inspiration for your holiday decking of the halls at the Nantucket Historical Association’s annual Festival of Trees. Inspired creations and interpretations of the holiday season’s most iconic symbol line the halls and exhibition spaces of the Whaling Museum. From the creative minds of over 50 local businesses, non-profits, and individuals, each tree is unique and is varied in its style and interpretation of the season. 

On Display: 

Whaling Museum
December 1–30
Mon–Sat, 10 am–4 pm
(Closed Christmas Day)

FREE for NHA members and Island Residents

Preview Party – SOLD OUT!
Thursday, November 30 from 6–8 pm, at the Whaling Museum

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 2023 Official Stroll Program click here for the ’22 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!

11:00AM-5:00PM MAIN STREET STAGE ENTERTAINMENT: Stop by the stage to enjoy eclectic performances by Theatre Workshop of Nantucket, The Dreamland’s Family Theatre Performs Madeline’s Christmas, Susan Berman & Ray Songs, NCMC Vocalist, The Accidentals & Naturals, and Victorian Carolers Songs!  

11:45AM TOWN CRIER RINGS IN CHRISTMAS STROLL! Gather at the Main Street stage to help our inimitable Town Crier ring in our 47th Stroll!

12:00PM-2:30PM SANTA CLAUS COMES TO TOWN! Watch Santa’s arrival via Coast Guard cutter, and join Santa’s parade as it travels up Main Street and across Centre Street to the NHA Whaling Museum (Santa will be traveling in a vintage fire truck this year!)

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.

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.

Please note the venue for this year: White Elephant Ballroom, 19 North Water Street

Dreamland Stroll Party Featuring The Hess Twins

The third annual Dreamland Stroll Party will be held on Friday, December 1st 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.

Jolly Jam, Skate With Santa

nantucket jolly jam

3:00PM – 6:00PM, Sunday, December 3

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

St. Paul’s Church Concert & Christmas Market


Book Signings at Mitchell’s

Sustainable Farmers Market at Nantucket Yacht Club

Nantucket Hotel Brunch with Santa

White Heron Theatre Company’s A Sherlock Carol

Tickets here. Friday, December 1 and Saturday, December 2, both at 7 pm

Theatre Workshop of Nantucket – Elin Hilderbrand’s Winter Street

Celebrate the season with The Quinns in the first-ever stage adaptation of Hilderbrand’s work. Tickets.

100 Mile Makers and Nantucket Resource Partnership present a Spicy Dance Party!

Boston Strings Academy

NCMC presents students from the Boston String Academy at St. Paul’s at 1pm and 6:30pm. Free.

Sugar Plum Social at Lemon Press