THE MOUSE TRAP

9/10-26

Bennett Hall

Step into the snow-bound world of Monkswell Manor and become part of theatrical history. Written by Agatha Christie, The Mousetrap opened in London in 1952 and holds the title of the world’s longest‐running play on the West End. Theatrenantucket.org

PRELUDE TO A KISS

9/6-18

In this must-see romantic comedy that Variety describes as "A powerful, genuine fairy tale," Rita and Peter's wedding day doesn't quite go as planned, after a mysterious elderly stranger kisses the bride and accidentally swaps souls with her. nantucketperformingarts.org

NANTUCKET ISLAND FAIR

9/12-13

Taking place at Tom Nevers Field, the annual two-day harvest festival highlights traditional county fair events such as a three-legged race, a livestock tent, artisans tables, local food, live music and even a watermelon-eating contest. nantucketislandfair.com

NANTUCKET COTTAGE HOSPITAL SANKATY SWING

9/14

Sankaty Head Golf Club

One of the premier athletic fundraisers of the shoulder season, the Sankaty Swing offers golfers an opportunity to experience one of the most scenic world-class courses on the East Coast. nantuckethospital.org

CROSS-ISLAND HIKE

9/19

Join the Nantucket Land Bank for the annual cross-island hike through the island’s sprawling conservation lands from Tom Nevers through the Middle Moors and out to Settler’s Landing in Madaket. The event is an incredible way to explore the island’s unique autumn ecology, far from downtown. nantucketlandbank.org

RACE FOR RECOVERY

9/27

Have some great family fun while supporting a most urgent need on Nantucket at Addiction Solutions' annual Race for Recovery 5K fundraiser. And since it's the organization's 10th anniversary, it is adding a 10k for those who feel up for that challenge. addictionsolutionsnantucket.org

RESTAURANT WEEK

9/28-10/4

Running the last week of September, this culinary tradition brings dozens of the island’s top eateries—from the high-end restaurants to casual dining establishments—together to offer special menus that highlight local flavors and ingredients. nantucketchamber.org

SCALLOPERS BALL

10/2

Nantucket Yacht Club

Hosted by the Nantucket Shellfish Association, this beloved local gathering celebrates the start of the island’s recreational scalloping season. The festive party features live music, cold drinks and endless spreads of fresh, locally harvested seafood. nantucketshellfish.org

NANTUCKET FASHION SHOW

10/10

Nantucket Hotel and Resort

An unforgettable night of style, the Nantucket Fashion Show brings the runway to the island. With designers and local businesses participating, the show is a great opportunity to see the latest fall trends. nantucketchamber.org

LOVE LETTERS

10/1-11

Bennett Hall

On the surface, Love Letters follows two lifelong correspondents as they exchange letters, postcards and valentine notes over decades. But for audiences who cherish nuance, good writing and the world of “old- Nantucket-meets-old-New England” sensibility, Love Letters offers something even richer. Theatrenantucket.org

NANTUCKET HALF MARATHON

10/11

On your mark, get set, go! Runners will get to take in 13.1 miles of scenic Nantucket countryside, and if you’re not racing, cheer on the runners as they push toward the finish line. nantucketathleticassociation.com

NANTUCKET SHORT FILM FESTIVAL

10/11

The Dreamland

Celebrating local filmmakers for 14 years, the Short Film Festival showcases artsy, musical, comedic and educational shorts of all varieties for a night at the Dreamland, with films made on or inspired by Nantucket. nantucketshorts.com

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

11/24-28

Whaling Museum

Haul out the holly! The Nantucket Historical Association’s annual Festival of Wreaths once again takes over the Whaling Museum to ring in the holiday season. For six days, the museum is adorned with dozens of decorative wreaths designed by local shops, restaurants, schools and nonprofits. Free for NHA members and island residents, with a 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

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