8 Magical Holiday Events to Enjoy in Nantucket

nantucket holiday events

nantucket tree 1Even though it’s winter, there’s no reason why Nantucket can’t be a great vacation destination. Our quaint little town comes alive with during the holiday season when it comes to the spirit and traditions of the holidays. Listed below are some lovely Nantucket holiday events that make Nantucket the perfect place to spend time this December.

8 Magical Nantucket Holiday Events:

Nantucket Christmas Stroll Weekend

Dec. 1-3 2023

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  • Location: Straight Wharf, 1 Steamboat Wharf, Nantucket, Ma
  • Time: 10:00 AM – 3:00 PM (Shops may be open later)
  • Cost: Free

The 2023 Christmas Stroll on Nantucket is back to bring Christmas cheer again. December 1-3, 2023 is the date for the 49th annual Christmas Stroll. This beloved Nantucket holiday event  occurs after Thanksgiving and is a week of holiday shopping. Start planning your trip now!

Local business owners initiated this event in 1973 to prevent islanders from traveling to Cape Cod for holiday shopping. You don’t want to miss this Nantucket holiday event!

Everyone enjoys the festive atmosphere along Main Street during this fun-filled event. Carolers sing on the streets, there is a 20-foot tree at the top of Main Street, craft shows, performances, and special dinner offers at local restaurants.

Santa will arrive on his nautical “sleigh” at noon on Saturday. There will be holiday activities, such as carolers in Victorian garb, the Magical Talking Tree, craft shows, and a European-style Christmas Marketplace.

Join in Nantucket’s holiday spirit while receiving some great discounts and enjoying food and drink at restaurants and bars.

For more information go to nantucketchamber.0rg

Nantucket Festival of Trees

Dec. 1 – 30, 2023

nantucket tree lightings and holiday festivals

  • Location: Whaling Museum, 13 Broad St, Nantucket, MA
  • Time: 10 AM – 4 PM, Monday-Saturday
  • Cost: Free for NHA Members and Island Residents

The Nantucket Historical Association’s annual Festival of Trees kicks off the Christmas season. The preview party will take place on November 30, 2023.

A preview party will take place at the Whaling Museum, and the display will remain up throughout December. The Nantucket Stroll weekend begins with this Nantucket holiday event.

Nantucket Festival of Trees presents community-designed trees created by local artists, groups, school children, local merchants, and nonprofit organizations.

Yuletide Fair

December 2, 2023

nantucket tree lightings and holiday festivals

  • Location: White Elephant Ballroom, 19 No Water St, Nantucket, MA
  • Time: 10 AM – 2 PM
  • Cost: Free

Since 1922, the Nantucket Lighthouse School’s Yuletide Fair has heralded the holiday season. The Yuletide Fair is a beloved community event featuring unique handcrafted holiday items, heirloom-quality gifts, a holiday bake shop, and holiday craft activities for children. We hope to see you there.

This beloved Nantucket holiday event wouldn’t be possible without the generous support of our local businesses and community members. Note location this year at White Elephant Ballroom.

A Sherlock Carol

Dec. 1-3, 2022


  • Location: White Heron Theatre Co, 5 N Water St, Nantucket, MA
  • Time: Starts at 7:00pm
  • Cost: varies
The white Heron will be hosting a dramatic reading  when Sherlock Holmes meets Charles Dickens’ beloved tale of A Christmas Carol. The full cast of the original New York production of A Sherlock Carol will come to Nantucket for 2 performances only on the weekend of the Nantucket Stroll.
A Sherlock Carol is written and directed by Nantucket’s favorite Mark Shanahan. The production is currently playing on London’s West End as well as other theaters throughout the country.
Come early for hot cider and cookies to enjoy the holiday spirit at the White Heron Theatre.

Madeline’s Christmas

Dec. 7-17th, 2023

  • Location:Dreamland Theatre, 17 So Water St, Nantucket, MA
  • Time: 2, 4 and 5:30 PM shows
  • Cost:  $30/ $25 members

Madeline’s Christmas -The Dreamland Stage Company will have plenty of performances of this Christmas classic from December 7th to 17th, so there is sure to be one that fits your busy holiday schedule.  This spunky Parisian child Madeline has delighted audiences of all ages for decades. This holiday season introduce your children to Madeline and her magic carpets, to help you count your blessings and set the mood for a magical holiday season.

Winter Street

Through Dec. 3rd, 2023

  • Location: Theatre Workshop, Bennett Hall, 62 Centre St, Nantucket, MA
  • Time: Starts at 7 pm
  • Cost: varies

Winter Street will play at the Theatre Workshop of Nantucket through December 3rd. This production is a new adaptation of Elin Hilderbrand’s novel, Winter Street. The beloved Nantucket novelist introduces us to the Quinn Family and follows them through the holidays with a couple of festive weddings and of course kept exciting with births, deaths and love – new love, old love, passionate love, but most importantly love!  This new Hilderbrand adaptation of the Quinns is sure to become a Nantucket holiday favorite.


Brunch with Santa

Dec. 17, 2023

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  • Location: The Nantucket Hotel & Resort,  77 Easton St, Nantucket, MA
  • Time: 11am – 2pm
  • Cost: reservation needed
Start a new holiday tradition the whole family will enjoy. Enjoy a magical delicious brunch with yummy favorites and visits with Santa himself during this wonderful Nantucket holiday event.

Red Ticket Drawing

December 24, 2023

  • Location: The Nantucket Chamber of Commerce, Nantucket, MA
  • Time: 3pm
  • Cost: Free

To encourage local shopping and sustainability of island commerce, the Nantucket Island Chamber of Commerce member businesses are giving out one red ticket to their customers, for every $25 spent.

This popular Holiday Red Ticket Program begins November 1st and culminates on on December 24th.  At 3pm, the 6 lucky winners of $1,000, and 1 extra-lucky winner of $5,000 will be drawn at random from the collection of tickets.


Relax, Unwind and Unplug in Nantucket

nantucket christmasThe holidays can be difficult when you can’t be with family or close to the end of a difficult year. Even though the holiday season is full of fun and merriment, it can also lead to stress and exhaustion! A winter weekend getaway to Nantucket is a great way to escape the hustle and bustle. Getaway for a romantic weekend, reconnect with friends, or go on a mid-week getaway to recharge. You can find peace and privacy in the cozy and elegant inns. Visit the local shops for bargains, wander the empty beaches, or unplug and read your favorite book. Enjoy some well-deserved time away with Nantucket holiday events!

We wish you a happy holiday season!   Browse our website for more information about Holiday Events on Cape Cod, Martha’s Vineyard or Plymouth.




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