A Time-Honored Tradition – Christmas Stroll on Nantucket

There is no better way to get into the holiday spirit than to book a trip to Nantucket for Christmas Stroll. Now in its 45th year, the special weekend brings a uniquely festive atmosphere to the island from November 30 to December 2. It is also the perfect occasion to create memories that will last a lifetime… and get a head start on holiday shopping in a merry environment.
Before we provide our very own suggestions to make the most of the joyful festivities, a history lesson on the origins of the weekend is in order. The time-honored tradition of Christmas Stroll started in 1973, when the founders of the original Nantucket Christmas Stroll tried to find ways to retain shoppers on Nantucket for holiday shopping. Merchants decided to incentivize islanders to shop local by keeping their stores open late the first Friday in December. That initial Stroll, christened by merchants as a “Christmas Shoppers Stroll” was a huge success. Shopkeepers entertained shoppers with wine, hot chocolate, tea, mulled cider, fruitcake, and holiday cookies while they perused crafts, books, clothes and wares, and other holiday gift items.
In the years that followed, the event started drawing large crowds and quickly gained a robust reputation nationally and internationally, becoming a not-to-be-missed holiday shopping event. Now, more than four decades later, Nantucket’s Christmas Stroll is still held the first weekend of December every year. The event is part of the Chamber of Commerce’s “Nantucket Noel,” and preparations begin just before Thanksgiving.
The day after Thanksgiving, hundreds of decorated seven-foot Christmas trees line downtown streets and are illuminated during a public ceremony with caroling at dusk. A local artist is chosen to adorn the huge 20-foot tree at the top of Main Street, a tree that “magically” talks to all who visit it during Christmas Stroll Saturday, on December 1.
That same day, carolers in costume sing familiar holiday tunes at various downtown locations. Main Street is vibrant throughout the weekend, with craft shows, live performances, special dinners at island restaurants, tours, exhibitions and more. Midday on Stroll Saturday, the Nantucket Town Crier will ring in the 45th Annual Christmas Stroll and will lead everyone to the wharves to meet Santa, who arrives via Coast Guard Cutter. Santa will walk down the wharf, and then ride to the Jared Coffin House downtown to meet with children.
Starting on November 30, the Nantucket Whaling Museum, steps away from Hotel Pippa, will be transformed into a sumptuous winter wonderland by the Nantucket Historical Association. Their Annual Festival of Trees showcases more than 80 Christmas trees designed and adorned with unique decorations – a must-visit for those on island during Stroll Weekend or during the holidays.
There is so much to see and do during Stroll Weekend – the Hotel Pippa team is available to schedule dinner reservations and recommend the best activities to make the most of the weekend. Island restaurants pull out all the stops during the special weekend, creating scrumptious feasts and delicious prix-fixe menus.
For the ultimate Stroll Weekend, our staff recommends:
  • • Tasting seasonal brews while listening to live music performances at Cisco Brewery
  • • Discovering the Christmas-decorated mansions of the Cliff & Brant Point via a unique walking tour loaded with historic commentary
  • • Cookie decorating at the Nantucket Cookie Company
  • • Participating in a wreath-making class in the Hayloft at Bartlett Farm
  • • Shopping for handcrafted gifts at the Christmas Stroll Market on Main Street
  • • Attending book signings with local and visiting authors at Mitchell’s Book Corner
  • • Checking out the latest productions at the White Heron Theatre
We look forward to welcoming you at Hotel Pippa for this magical weekend and to kick off the holiday season in a festive atmosphere.