NANTUCKET SHORT FILM FESTIVAL

October 11

Dreamland

Since 2013, NCTV’s signature Nantucket Shorts Festival has shined a spotlight on local filmmakers, with a wide selection of comedy, drama and nonfiction films shot on Nantucket and inspired by the island. nantucketshorts.com



FESTIVAL OF WREATHS

November 24-29

Whaling Museum

One of Nantucket’s most recognizable properties transforms into a winter wonderland for the Nantucket Historical Association’s annual Festival of Wreaths. For six days only, the museum will be adorned with dozens of decorative wreaths designed by local shops, restaurants, schools and nonprofits. Free for NHA members and island residents. nha.org

A CHRISTMAS STORY, THE PLAY

November 25-December 14

Theatre Workshop of Nantucket

You probably already know Ralphie Parker and his quest for a genuine Red Ryder BB gun, though you probably haven’t seen the holiday classic told on stage. This year, Theatre Workshop of Nantucket’s winter play is none other than Jean Shepherd’s A Christmas Story, the heartwarming and addictively funny Christmas staple that’s sure to be a holiday hit. theatrenantucket.org

COLD TURKEY PLUNGE

November 27

Children's Beach

For the 24th year, the Nantucket Atheneum’s Cold Turkey Plunge is back, daring children and adults alike to brave the cold waters at Children’s Beach for a quick dip on Thanksgiving morning. Dress up in your best Thanksgiving outfit, wetsuit or bathing suit, while supporting a good cause. Proceeds benefit the Atheneum’s Weezie Library for Children and its free, year-round programming. (10 a.m.) nantucketatheneum.org

CHRISTMAS TREE LIGHTING  CEREMONY

November 28

As downtown Nantucket embraces the holiday spirit with decorated trees lining the streets, there’s no Christmas tree as big or as bright as the one at the top of Main Street. That tree will be lit at 4 p.m. on the day after Thanksgiving to the tune of Christmas carols, officially kicking off the holiday season. nantucketchamber.org

HOLIDAY WORKS EXHIBITION

November 21-December 24

Artists Association of Nantucket

The Artists Association of Nantucket’s Holiday Works exhibition offers everything from the perfect stocking stuffer to a Yuletide masterpiece. Check out works from local artists at the AAN’s Cecelia Joyce and Seward Johnson Gallery at 8 Federal Street, with a Holiday Open House reception on December 5 from 4-7 p.m. nantucketarts.org

51st ANNUAL CHRISTMAS STROLL

December 5-7

‘Tis the season. Whether you’re on the island year-round or just visiting for the weekend, Christmas Stroll is the best opportunity to experience Nantucket in the winter while supporting local businesses. Originally an effort to promote shopping locally after the development of the Cape Cod Mall, Stroll has become the thing to do each winter, with craft shows, holiday deals, live entertainment and even a visit from Santa Claus. nantucketchamber.org

DECK THE WHARF BASH

December 5

Straight Wharf Fish

An evening of luscious bites and bubbly—including Champagne and caviar—the Maria Mitchell Association’s Deck the Wharf Bash is a time to mingle and jingle along the harbor during the Saturday of Stroll. Celebrate a holiday photobooth, reindeer raffle, cosmic caroling and plenty of caroling. mariamitchell.org

FESTIVAL OF TREES

December 5-31

Whaling Museum

The Nantucket Historical Association’s annual Festival of Trees cannot be missed. Check out the Whaling Museum’s galleries as they’re loaded with beautiful and truly unique Christmas trees, including traditional greens, ornate whites and anything in between. Free admission for island residents and NHA members. nha.org

LIGHTHOUSE SCHOOL YULETIDE FAIR

December 6

Straight Wharf Fish

Now in its 20th year, the Nantucket Lighthouse School’s Yuletide Fair offers decorative crafts, local artwork, baked goods and much, much more on the Saturday morning of Stroll weekend. Warm up in the White Elephant Ballroom for a wide assortment of holiday gifts and stocking stuffers, as well as craft activities for children. nantucketlighthouseschool.org



NEW YEAR'S EVE GALA

December 31

Nantucket Hotel

Ring in the new year at the Nantucket Hotel. This year, the hotel features a three-course New Year’s Eve dinner, a mind-reading performance and an after party in the hotel’s Breeze restaurant, where you can dance the night away and into the early hours of 2026 with DJ Billy Voss. thenantuckethotel.com