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2019 Nantucket Chamber Christmas Stroll Weekend

Catch a flight to celebrate all things merry and bright!

ACK SantaRing in the holiday season by strolling the bedecked streets of the Gray Lady from December 6th through December 8th, 2019.

Now in its 46th year, the Nantucket Chamber Christmas Stroll Weekend is an enchanting, magical tribute to holidays past. Witness as downtown Nantucket is transformed into a winter wonderland featuring hundreds of decorated Christmas trees, illuminated during a public ceremony and complete with with carolers in costume.

Each year a local Nantucket artist is chosen as decorator, tasked with the honor of adorning the 20-foot tree that will shine as a seasonal beacon at the top of Main Street. The festivities don't stop there — from craft shows and live entertainment to historical tours, exhibitions and special dinners at beloved island restaurants, the entire island comes together to bring the spirit of the season alive for residents and visitors alike.

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Plan your Nantucket Stroll Weekend trip with these must-see and do activities:

  • Nantucket's Own Christmas Marketplace: Meander through a wonderous Christmas Market and celebrate the enchantment of the giving season. Browse specialty items such as handcrafted gifts and merchandise created by local artisans, businesses and non-profits.
  • "People's Choice Award" Storefront & Tree Decorating Contest: Admire the carefully decorated storefronts and trees as you walk the streets of the Gray Lady. Cast your vote for your favorites!
  • Magical Talking Tree: Children young and old have been mesmerized by Nantucket's mysterious Talking Tree! Nestle close to its branches and cast your wish for the holiday season.
  • Santa Claus' Arrival: No holiday stroll is complete without the gran arrival of the man in red! Watch as Santa Claus makes his way to the island via Coast Guard cutter and join him as he travels up Main Street for the annual stroll parade. 

Traveling to Nantucket for Christmas Stroll Weekend

Beat the ferry, rise above traffic and tolls, and get to ACK faster with frequent flights from Cape Air. Cape Air offers direct service to Nantucket from Boston, Hyannis, New Bedford and New York City – with our now daily, year-round flights from JFK! Reserve your seat on a Cape Air flight to Nantucket, today.