Yesterdays Island, Todays Nantucket

Holiday Magic

More than 50 years ago, the originators of the first Nantucket Christmas Stroll were trying to encourage island residents to do their holiday shopping locally instead of traveling across Nantucket Sound to shop at malls on Cape Cod.

That first year—1973—island merchants kept their shops open late the first Friday in December, offering wine, hot chocolate, mulled cider, and holiday treats to shoppers as they greeted their neighbors and shopped for holiday gifts. That evening, christened as a “Christmas Shoppers Stroll,” was a mere three hours in duration and was a huge success.

In subsequent years, the event grew exponentially, drawing larger crowds until it evolved into a nationally- and, ultimately, internationally-renowned holiday event. Now organized by the Nantucket Island Chamber of Commerce, the popular and festive Nantucket Christmas Stroll is typically held during the first full weekend of December.

This year’s Stroll is being celebrated as the 50th because the events was canceled one year during the pandemic. The 2024 Nantucket Christmas Stroll will feature more than 150 decorated 6-foot holiday trees set along downtown streets, along with a 20-foot tree at the top of Main Street. All these trees will be lit up at dusk the day after Thanksgiving during a special Illumination Ceremony led by Nantucket’s Town Crier: a fun family gathering with caroling.

“As we celebrate this momentous 50th anniversary, we’re reminded of the spirit of community and togetherness that has made the Nantucket Christmas Stroll a beloved tradition for generations,” said Peter Burke, Executive Director of the Nantucket Island Chamber of Commerce. “We’re excited to honor our past while creating new memories for the next 50 years.”

Another annual Nantucket tradition that coincides with Stroll is the Nantucket Historical Association’s Festival of Trees. Opening to the public on Friday, December 6, the Whaling Museum at 13 Broad Street is transformed into a glittering winter wonderland with dozens of trees designed and decorated by local businesses, artists, individuals, and non-profit organizations. For details on this month-long display and other NHA holiday and winter events, visit nha.org.

Many begin to gather downtown on December 7—Stroll Saturday—around 9 am for coffee and breakfast. Shopping at St. Paul’s Christmas Stroll Market starts at 9:30 am at 20 Fair Street, with their lunch from 11:30 to 2 pm. At 10 am, the Chamberorganized Stroll Marketplace opens, featuring stalls selling food and beverages alongside vendors selling holiday gifts, crafts, art, and more until 3 pm. The Methodist Church at 2 Centre Street opens their Christmas Café at 10 am, and public is invited to climb the tower at the First Congregational Church for the best view of Nantucket from 10 am to 12 noon.

Live entertainment on a stage set up on Main Street begins in the morning and continues through the day, along with strolling carolers and the Talking Christmas Tree at the top of Main Street. At 12 noon, Nantucket’s Town Crier announces the arrival Santa Claus by boat and leads a parade through downtown with the Big Man in Red riding on The Nantucket Hotel & Resort’s antique fire truck before Santa visits with children.

On Sunday, December 8, Nantucket Dance Theatre will hold performances of the Nantucket Nutcracker at 2 pm and at 5 pm. This family-friendly holiday show features local youth dancers: tickets at NantucketDanceTheater.org

In addition to the Chamber’s Stroll events, island businesses offer walking tours, book signings, art shows, nature hikes, special sales, raffles, holiday theatre performances, concerts, and stroll receptions to fill your weekend schedule. For up-to-date details of this year’s events, visit the Insider’s Guide to Nantucket: Nantucket.net.

Christmas Stroll is a celebration of the holiday season, but it is our island’s warm welcome and the magic of Nantucket that promises to warm your hearts.

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