In 1973, local businesses founded the Nantucket Christmas Stroll in an effort to prevent islanders from fleeing to Cape Cod to do their holiday shopping. Now, 45 years later, the annual event acts as a draw for tourists from all over the Northeast. Held the first weekend in December, hundreds of decorated seven-foot Christmas trees are illuminated while carolers sing familiar holiday tunes and merchants offer special deals and refreshments to customers.
The celebration kicks off the holidays in Nantucket, while also serving as the start of the Nantucket Historical Association’s Annual Festival of Trees, which showcases more than 80 Christmas trees adorned with unique decorations. Held at the Nantucket Whaling Museum, the festival transforms the historic space into a glittering winter wonderland for the entire month of December. A celebration of the community, the event features trees crafted by local merchants, nonprofit organizations, artists, and children.
If you miss the last ferry home, a romantic stay at the historic White Elephant Hotel is sure to round out your Nantucket experience. The waterfront resort is within walking distance to downtown and will be aptly lit for the holiday season. Its eatery, Brant Point Grill, even has a special menu for Stroll Weekend. Be sure to order with a Nantucket Mule, complete with 888 Cranberry Vodka, ginger beer, and cranberry juice.