Christmas Stroll Weekend Returns to Nantucket Island

The 47th annual Nantucket Christmas Stroll will be celebrated the weekend of December 3-5, 2021. Many festive activities are planned. Details at Insider's Guide to Nantucket:

Nearly 50 years ago, the originators of the first Nantucket Christmas Stroll were trying to prevent islanders from traveling to Cape Cod, 30 miles across Nantucket Sound, to do all their holiday shopping.

Rewind to 1973, a year when local merchants kept shops open late that first Friday in December, inviting locals to do all their holiday shopping on-island. That evening, christened as a “Christmas Shoppers Stroll,” was a mere three hours in duration and 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 subsequent years, the event grew exponentially, drawing larger crowds until it became a nationally- and, ultimately, internationally-renowned holiday event.

Last year, the annual Nantucket Christmas Stroll was cancelled due to pandemic restrictions, but for 2021, this popular and festive event, now organized by the Nantucket Chamber of Commerce, is planned for the weekend of December 3, 4, and 5.

This year’s Nantucket Christmas Stroll, with a theme of “Holiday Traditions,” will feature dozens of decorated holiday trees mounted throughout the downtown area, 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 (Friday, November 26) with a special Illumination ceremony led by Nantucket’s Town Crier, with caroling. The public is invited, and the event will be live-streamed on Facebook and Instagram @ACKChamber.

Once again this year, the Nantucket Historical Association is transforming their Whaling Museum into a glittering winter wonderland. Throughout the month of December starting on the 3rd, more than 50 uniquely decorated and crafted trees designed by local businesses, artists, individuals, and non-profit organizations make up the Festival of Trees showcase. For 2021, in addition to the display, the NHA is hosting three Family Nights at the Festival of Trees from 4pm to 6pm on December 10, 14, and 21, featuring live entertainment by local musicians and dancers.

In addition to its longstanding traditional events, the Nantucket Island Chamber of Commerce has announced weekend highlights and new activities on Stroll Saturday that include: the sale of 47th Annual Stroll pins and merchandise; Storefront and Tree Decorating Contests; Santa’s Village from 10am to 3 pm featuring food, crafts, beverages; Elementary School Art Show; eclectic entertainment on the Main Street Stage; and the arrival by boat of Santa Claus; and special holiday theatre performances. Island business people are offering cookie decorating, walking tours, book signings, hikes, special sales, concerts, and stroll receptions. And don’t miss the Santa Pub Crawl on December 5 from

Most of the events will be held on Saturday, December 4: for exact details, dates, times, and locations, visit and the Insider’s Guide to Nantucket.

Over the decades, the Nantucket Chamber of Commerce has elarged and improved up their Christmas Strolls, but the holiday spirit and feeling of fellowship on the island adds warmth and hospitality to the festivity of the holiday season on Nantucket Island.

Check the Insider’s Guide to Nantucket Calendar of Events for specific dates and times of holiday events on Nantucket Island.

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