22 Nov 2023

Nantucket Christmas Stroll 2023: Everything You Need To Know

Nantucket Christmas Stroll 2023
Nantucket Christmas Stroll 2023

📷 @nantucket_magazine

There’s no place like Nantucket for the holidays! The Tree Lighting on Main Street is just around the corner, marking the official start of the holiday season on the island. This tradition is just the first of so many fun and festive events that you don’t want to miss — including one of our all-time favorites, the Nantucket Christmas Stroll. From sporting your favorite ugly sweater to supporting local Nantucket shops, it’s a weekend filled with joy, laughter, and lots of holiday cheer. So take a look at everything you need to know about Stroll weekend!

Nantucket Christmas Stroll

📷 @nantucketmagic

Nantucket Holiday Stroll

📷 @nantucketmagic

So, When is The Nantucket Christmas Stroll?

The 49th-annual Nantucket Christmas Stroll will be held on December 1-3. Organized by the Nantucket Chamber of Commerce, this highly-anticipated event features fun activities throughout the weekend to bring the community together, show support for local businesses, and get islanders & visitors alike in the holiday spirit.

Where to Stay For Christmas Stroll

Many Nantucket hotels close during the winter season, so it’s a great time of year to rent — plus, it’s a perfect way to take in all the island has to offer. The Lee Real Estate team always has a variety of short and long-term rentals available, so take a look at our current rental properties and reach out to our team for more information!

Fun Events to Check Out Throughout the Weekend

There are so many Stroll events to look forward to this year, but here are a few can’t-miss festivities on our list:

Nantucket Christmas

📷 @nantucket_cultural_district


St. Paul’s Christmas Stroll Concert

Kick off your Stroll weekend at the St. Paul’s Church holiday concert on Friday, December 1st at 7:00pm. Listen to beautiful holiday classics and even participate in some fun holiday caroling.


The Stroll Party

If dance music is more your thing, head to the Dreamland Stroll Party featuring the well-known DJ duo, the Hess Twins! Enjoy a photobooth, some drinks, and light bites as well.


Santa’s Village

On Saturday, December 2, you can stroll through Santa’s Village from 10:00am-3:00pm and indulge in delicious food and drinks, find handcrafted gifts, and take in the enchanting decorations.


Ugly Sweater Contest

Show up in your ugliest holiday sweater and get judged by Santa Claus himself! The ugly sweater contest starts Saturday, December 2 at 3:00pm, but contestants should arrive by 2:30pm.


Festival of Trees

Head to the Whaling Museum for the Festival of Trees to enjoy magnificent Christmas trees designed by community members, local merchants, nonprofit organizations, artists, artisans, and children. Our team will have a tree decorated there this year, let us know if you spot it!


Artists Association Pop-Up

Looking for a last-minute gift? Shop local art at the Artists Association pop-up throughout the weekend in the Big Gallery, located upstairs at 12 Straight Wharf. For even more gift ideas, be sure to stop by Susan Lee’s gallery (located right next to the Lee Real Estate Office) to browse beautiful photographs that would make the perfect present for any Nantucket lover.

Nantucket at Christmas

📷 @nantucketmagic

Even More Christmas Stroll Fun To Get In On

– Head to Brant Point Lighthouse to see it decked out with a beautiful (and big!) Christmas wreath.

– Shop all of the Christmas markets and fairs throughout the weekend to find beautiful and local artisan-made gifts for everyone on your list.

– Walk along Easy Street and take a look at the Dory Boat that displays a cute little Christmas tree in the harbor.

– Support local shops on Main Street while enjoying dozens of individually decorated trees and window boxes lining the street. You could even catch the carolers popping in to perform on Main Street throughout Saturday’s festivities!

– Collect red tickets throughout your holiday shopping for your chance to win big at the Annual Christmas Eve Drawing! The Nantucket Island Chamber of Commerce is continuing their tradition of the Holiday Red Ticket Program, where you can receive one ticket for every $25 spent at a participating local business. On Christmas Eve, one lucky winner will be chosen at random to receive $5,000! Not going to be on the island for Christmas? No worries — you can also donate your red tickets to one of Nantucket’s local non-profits and give them a chance at a holiday boost in their funding!


As you can see, the Nantucket Christmas Stroll is a tradition you don’t want to miss. We always love seeing our clients out and about during this fun holiday weekend spending time with family and friends, and supporting local businesses.

If you’re looking for a place to stay during Stroll, later this winter, or next summer, we’re always here to help! Reach out to our team today by sending an email to, or give us a call at 508-325-5800.

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