This Iconic Holiday Event in Massachusetts is the One Thing You Must Do This Season

Ever since I started reading Elin Hilderbrand's beach novels like “The Perfect Couple” and “Winter Street,” I have become obsessed with all things Nantucket. Pristine beaches, quaint inns, delicious seafood, and a rich history make this former whaling community a very unique travel destination. While most people consider Nantucket a place to visit in the summertime, the island is also a fantastic spot to celebrate the winter holiday season. The town’s best-known holiday event is their annual Christmas Stroll and this year’s festivities promise to be extra special. 

Winter 2024 is the 50th anniversary of the Nantucket Christmas Stroll weekend. This year’s stroll will take place from Dec. 6-8 and will include music, live performances, shopping, and some special guests. The much-anticipated event is presented by the Steamship Authority.

The highlight of the festivities takes place just before noon on Saturday. At this time, a town crier will announce the arrival of Santa Claus who will be brought to Nantucket's Straight Wharf via a Coast Guard Cutter. He will then parade through town and later take pictures with children and families at the local Whaling Museum.

Saturday is also a great time to do some holiday shopping. The festive Christmas Stroll Marketplace will take place from 10 a.m. to 3 p.m. The European-style market will feature a wonderful selection of handmade crafts, jewelry, Chamber of Commerce merchandise, beverages, and delicious food.

Other festive events include a hilarious ugly sweater contest, a magical talking tree display, concerts, historical and literary walking tours, a scavenger hunt, and a popular Christmas House tour. There are even several opportunities to see a live version of Elin Hildrenbrand’s novel, “Winter Street.” 

And it wouldn’t be a stroll weekend without carolers. A holiday sing-along with these talented Victorian-clad performers is like a scene in a quintessential New England Christmas movie. 

To get to Nantucket, you will have to fly or take the ferry, so be sure to make your travel plans as soon as possible as this holiday weekend is sure to be a popular one on the island.

Have you attended a past Christmas Stroll weekend? If so, please tell us all about your holiday experience. You can find even more information about this fantastic event at the Nantucket Island Chamber of Commerce website and the Nantucket Island Chamber of Commerce Facebook page. And if you are interested in even more Christmas fun, I suggest visiting these festive Massachusetts destinations and colorful local holiday light shows.