Your Best Holiday Season on Nantucket 

Your Best Holiday Season on Nantucket 

Picture this: You’re standing on Main Street with a single red ticket in your hand, and the crowd around you is cheering as the town crier begins to read the winning numbers that will put $5,000 in one lucky ticket holder’s pocket. It’s Christmas eve on Nantucket, and as you look at all the joyful faces around you at the Annual Red Ticket Drawing, you understand it’s actually not at all about the money - in fact, most winners typically donate the funds to their favorite charity. Instead, it’s about the giving of the season, the small town-feel that is alive and well on this island, and the overwhelming gratitude for being surrounded by the amazing people of this community. The town crier begins to read, and the numbers are matching yours… but let’s start back at the beginning. 

This Thanksgiving 

Unlike the rest of America, Thanksgiving on Nantucket is quiet, unhurried and restful. Dig in on a locally sourced turkey from Bartlett’s Farm (they offer a prepared menu, too) or do as the First family does and get the entire meal from local favorite Fairgrounds Restaurant, but it’s what else you do this day that is really special. We prefer taking a hike through the moors - a favorite is Sanford Farm, located on Madaket Road. Here, four miles of trails lead to the wild southern shores of the island, and work up quite an appetite. You can find more trails by visiting, our favorite place to find hikes identified by different lengths and terrain. The best part? Coming home to the smell of a terrific meal.

The Tree Lighting Ceremony  

Black Friday on Nantucket is known as “Shop Local Day,” and there will be sales and specials at nearly every shop in town, but don’t miss the annual tree lighting ceremony at the top of Main Street which begins at 4 pm, and is often accompanied by President Biden and family. The community circles the impressive tree outside the Pacific Bank and carols are sung - making it an ideal experience for the whole family. 

Christmas Stroll

Nantucket wastes no time in getting into the Christmas spirit, with Christmas Stroll Weekend just on the heels of the Thanksgiving Holiday, that following weekend. Many summertime and seasonal restaurants re-open their doors, the sidewalks are crowded with people adorned in their most exuberant holiday garb (think Santa hats, gingerbread-patterned suits and elf ears on any discernible adult) and lit Christmas trees line the streets of downtown. Santa himself even makes an appearance (arriving by boat, of course) and greets children at noon that Saturday. Best of all, shops will host sales and specials, and are sure to have the perfect gifts for everyone on your list. 

Annual Red Ticket Drawing 

Finally, we’re back to you and that single red ticket, waiting patiently at the foot of the stage where the town crier announces the winning numbers. To receive a red ticket to participate, you’ve had to make a $25 purchase at a participating local store between November 1st through December 23rd, and there will be five lucky people to win $1,000, and just one extra lucky person to win the grand prize of $5,000. But it’s in that moment that you undoubtedly realize that you’ve already won what matters most, time celebrating the best holiday season ever on this beautiful island of Nantucket.

New Year’s Eve

Now that the anticipation of the holidays have passed, New Year’s Eve on Nantucket is often quiet, serene, even mellow, with most locals and visitors gone to celebrate with family in other parts of the world. Expect empty beaches and just a few cars on the streets, but this is not to say fun can not be found on this final and jovial day of the year on Nantucket.

Many restaurants will offer special dining hours and menus, live music and entertainment - be sure to check the website of your favorite establishment to see if they’re participating. We do love the annual gala held in the ballroom of The Nantucket Hotel, where they ring in the new year twice (at 10 pm and midnight) so you never miss out on the fun. You can purchase tickets to attend at

Or, cook that celebratory meal yourself - we love BRIX Wine Shop Nantucket on Surfside Road for their selection of fine wines and cheeses, and for the main meal, Nantucket Meat & Fish Market on Old South Road will have you covered with an array of impressive meats and the perfect sides to accompany them.

The next day, set your alarm to catch the sunrise- we promise you won’t regret it, if not only for the bragging rights to friends that you were the first (as Nantucket is) to see the light of day in the new year on this far eastern island 30 miles out to sea. And that is what we call starting the new year off right.

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