FALL FESTIVAL & BATACULAR BIKE RACE

10/25

Milestone Cranberry Bogs

The Nantucket Conservation Foundation’s free fall festival combines family-friendly autumn classics with a trail bike race through the Middle Moors. If you’re not racing, check out the hayrides, live music, games and live performances. nantucketconservation.org

MAIN STREET HALLOWEEN PARADE

10/31

The Main Street Halloween Parade is a must-see the evening of Halloween, when the historic cobblestone streets close to vehicles as hundreds of adults, children and pets parade through town to show off their costumes. Awards will be given out for best in show followed by trick-or-treating at local storefronts.

FESTIVAL OF WREATHS

11/24-12/5

Macy Warehouse

Haul out the holly! The Nantucket Historical Association’s annual Festival of Wreaths has moved to the Macy Warehouse on Straight Wharf, to ring in the holiday season. For six days, the NHA property is adorned with dozens of decorative wreaths designed by local shops, restaurants, schools and nonprofits. Admission is free to all visitors. Tickets are available to the NHA's Festival of Wreaths preview party on November 23. nha.org

ELIN HILDERBRAND'S WINTER STREET

11/24-12/6

Theatre Workshop of Nantucket

Back by popular demand, Winter Street returns to Bennett Hall to close out Theatre Workshop of Nantucket’s 70th season on the island. The adaptation of Elin Hilderbrand’s 2014 novel Winter Street follows the Quinn family through holiday magic, weddings, insider trading, new loves, old loves and lots of laughs. theatrenantucket.org

COLD TURKEY PLUNGE

11/26

Children’s Beach

Support the Nantucket Atheneum in the 25th annual Cold Turkey Plunge at Children’s Beach, a festive event daring children and adults alike to brave the frigid harbor waters in a wetsuit or bathing suit for a quick dip at 10 a.m. on Thanksgiving morning. Proceeds support the Atheneum’s Weezie Library for children and its free, year-round programming. nantucketatheneum.org

CHRISTMAS TREE LIGHTING CEREMONY

11/27

As downtown Nantucket embraces the holiday spirit with more than 150 decorated trees lining the streets, there’s no Christmas tree as big or as bright as the one at the top of Main Street. At 4 p.m. on the Friday after Thanksgiving, that tree will be lit to the tune of Christmas carols, officially kicking off the holiday season. nantucketchamber.org

HOLIDAY WORKS EXHIBITION

11/19-12/24

Artists Association of Nantucket.

The Artists Association of Nantucket wraps up its 2026 season with its annual Holiday Works exhibition, offering everything from the perfect stocking stuffers to Yuletide masterpieces. 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 4 at 5 p.m. nantucketarts.com

A BROADWAY WHITE CHRISTMAS

11/27-29

Theatre Workshop of Nantucket invites audiences to celebrate Thanksgiving weekend with A Broadway White Christmas, a festive installment of its On With The Show cabaret series. theatrenantucket.org

CHRISTMAS STROLL

12/4-6

Whether you’re on the island year-round or just visiting for the weekend, Christmas Stroll is the perfect opportunity to experience Nantucket this holiday season, all while supporting local businesses. Over the past 52 years, Stroll has become the preeminent off-season weekend on the island, with craft fairs, a magical talking tree and a visit from Santa himself. nantucketchamber.org

DECK THE WHARF BASH

12/4

Straight Wharf Fish

The Maria Mitchell Association’s holiday party is back for its third year, taking over Straight Wharf Fish on the Friday of Stroll. Try extravagant bites, caviar and burgers from the team at Straight Wharf, while raising a glass of champagne and rocking around the Christmas tree in support of the Maria Mitchell Association's year-round programming. mariamitchell.org

FESTIVAL OF TREES

12/4-31

Whaling Museum

The Nantucket Historical Association’s annual Festival of Trees is back this December, transforming the Whaling Museum and the Candle Factory into a winter wonderland of unique and beautifully decorated trees. Free admission for island residents and NHA members, with a preview party December 3. (Closed Christmas Day) nha.org

LIGHTHOUSE SCHOOL YULETIDE FAIR

12/5

White Elephant Ballroom

The Nantucket Lighthouse School’s annual Yuletide Fair offers everything from handmade crafts, heirloom gifts and local artwork, to a holiday bake shop, warm hot chocolate and can’t-miss festive activities for children. You’ll be sure to find something at the fair at the White Elephant Ballroom. nantucketlighthouseschool.org

NEW YEAR'S EVE GALA

12/31

Nantucket Hotel

An elegant way to welcome 2027, the Nantucket Hotel’s New Year’s Eve Gala provides a chef-curated three-course a la carte menu, caviar, oysters, fine wines and live piano music. After dinner, dance the night away at the hotel late-night party, with hors d’oeuvres, drinks and a DJ set to enter the new year in style. thenantuckethotel.com