1. ELF, THE MUSICAL

NOVEMBER 21-DECEMBER 9

Bennett Hall

The best way to spread Christmas cheer is singing loud for all to hear! At least, that is, according to Buddy the Elf. Celebrate with everyone’s favorite holiday character in Elf, The Musical, performed by the Theatre Workshop of Nantucket. Based on the 2003 cinematic hit, it’s bound to leave everyone with a hearty dose of holiday cheer, nostalgia and laughs. theatrenantucket.org

2. FESTIVAL OF WREATHS

NOVEMBER 21

Whaling Museum

Celebrate community and artistic excellence at the Festival of Wreaths. These exquisite wreaths are crafted by local artists and designers, representing the holiday season’s beauty and generosity. The wreaths can be bid on through a silent auction, with proceeds supporting a cherished local charity, turning this festive event into a heartwarming gathering of neighbors and friends. nha.org

3. COLD TURKEY PLUNGE

NOVEMBER 23 AT 10:00 AM

Children’s Beach

Dare to start your Thanksgiving Day with a thrilling plunge into the crisp Atlantic waters during the annual Cold Turkey Plunge. A tradition for locals and adventurous visitors, this lively event promises laughter, excitement and a holiday experience like no other. nantucketatheneum.org

4. ANNUAL CHRISTMAS TREE LIGHTING & COMMUNITY CAROLING CEREMONY

NOVEMBER 24, 4 PM

Main Street

Gather under the twinkling stars at Main Street for the magical tree lighting ceremony. With the flip of a switch, over 150 trees will burst with colorful lights, illuminating the night sky. Join fellow islanders and visitors in caroling, and let the season’s joy warm your heart. nantucketchamber.org

5. HOLIDAY SMALL WORKS

NOVEMBER 24-DECEMBER 22

Artists Association Gallery

Experience the richness of Nantucket’s artistic community at the Artists Association Holiday Small Works exhibition. This cherished annual event showcases a diverse collection of small-scale artworks, all crafted with exceptional skill and creativity by local artists. Ideal for finding unique gifts or adding to your art collection, these pieces capture the essence of the holidays. nantucketarts.org

6. FESTIVAL OF TREES

NOVEMBER 30

Whaling Museum

The annual event kicks off the island’s Stroll weekend with community-crafted trees designed by local merchants, nonprofit organizations, artists and children. Peruse the sparkling trees within the Whaling Museum—you might gather some inspiration for your own! nha.org

7. THE STROLL PARTY

DECEMBER 1, 7 PM

Nantucket Dreamland

With music by the Hess Twins, rock out to the holiday season with lite bites, a photobooth, cocktails and plenty of fun. nantucketdreamland.org

8. 49TH ANNUAL CHRISTMAS STROLL WEEKEND

DECEMBER 1-3

Downtown Nantucket

Step into a winter wonderland during the Stroll Festival in downtown Nantucket. From twinkling lights to joyful carolers, this festive event marks the start of the holiday season on the island. Enter the ugly sweater contest, shop Santa’s village and meet Saint Nick himself as he arrives via nautical sleigh at noon on Saturday. nantucketchamber.org

9. NEW YEAR’S EVE PARTY

DECEMBER 31, 8 PM - 1 AM

The Nantucket Hotel

Dress your best and ring in the new year with The Nantucket Hotel’s annual gala— dancing, dinner and a great start to 2024 is promised with hosts DJ Billy Voss and Adam Dread. thenantuckethotel.com

10. COMMUNITY GAME SHOW

JANUARY 27, 2024, 7 PM

Nantucket Dreamland

Compete for cash prizes during Nantucket’s curated version of Jeopardy. To apply to be a contestant, email josh@nantucketdreamland.com. nantucketdreamland.org