Halloween: Nantucket does Halloween right—especially if you have kids! Main Street closes, all of the stores hand out candy （good candy!）， and there’s a costume parade. There’s also a haunted house at the old fire station.
Thanksgiving: Thanksgiving on Nantucket has traditionally been celebrated by the Turkey Plunge at Children’s Beach, which benefits the Nantucket Atheneum. Yes, people go into the water, no matter the weather. （Full disclosure: I have never done it.） The other Thanksgiving event happens on Friday. Everyone gathers downtown for the tree lighting. Nantucket’s streets are lined with Christmas trees that will later be decorated by classes at the elementary school and the nonprofits. At five o’clock there is a little ceremony and then the switch is flipped and all the trees light up at once! We sometimes have visiting dignitaries for this!
Christmas Stroll: The biggest holiday in the off-season and possibly all year is the Nantucket Chamber of Commerce’s Christmas Stroll （known simply as “Stroll,” as in “Elin is signing at four thirty the Saturday of Stroll”）。 We already know that the trees are lit, and as you might guess, the shop windows are festively decorated. The Killen family places a Christmas tree in a dory at the Easy Street Boat Basin. （Did you even go to Stroll if you didn’t photograph the Killen dory?） Traditionally, the Nantucket Historical Association throws a benefit party to preview its “Festival of Trees” display in the Whaling Museum. This is my favorite party of the year （sadly, it was canceled in 2020 and 2021）。 I describe this party in, you guessed it, my novel Winter Stroll. However, the Festival of Trees exhibit is open to the public through the new year and should not be missed—businesses and creative islanders decorate trees that are displayed throughout the museum.
On the Saturday of Stroll, Main Street closes. Santa arrives on a Coast Guard vessel at noon, and children can visit with him in the Methodist church. There are Victorian carolers. There’s a food tent in the Stop and Shop parking lot at the bottom of Main Street. In years of yore, you would see ladies from New York in magnificent fur coats. Now people tend to dress up as Buddy the Elf and the Grinch and naughty Mrs. Claus. There are book signings at Mitchell’s throughout the day. There are live bands at Cisco Brewers. Not every restaurant is open, so it’s very important to make dinner reservations way in advance—most restaurants start taking these reservations after Columbus Day.
One of my readers from Jacksonville, Florida, Jenna T., compiled a super-helpful list of Stroll tips. She mentions getting the Stroll Scarf—there’s a new scarf created every year, and the official one can be purchased only at the Nantucket Boat Basin Shop. She recommends B-ACK Yard BBQ on Lower Main as a great place to get drinks as you watch for Santa’s arrival. She and her crew had lunch at the Corner Table Market, a lovely spot for sandwiches, pastries, prepared foods, and coffee. Jenna loved the front porch of the Nantucket Hotel for drinks and the indoor Breeze restaurant for lunch or dinner. Jenna recommends booking your hotel early and reminded me that, as at the Hotel Nantucket, there is a three-night minimum over Stroll.
The proper greeting is “Happy Stroll!” Thanks, Jenna!
Giving Back
If you’ve visited Nantucket, you’ve already done your share by plumping the local economy with your hard-earned dollars. （And as you’ve learned, Nantucket is not cheap!） However, if you’re inclined to give even more, I will share my favorites of the Nantucket-based nonprofits. The three places I’m suggesting are extremely beneficial to the year-round community, including the workforce who clean your rooms, wash your dishes, prune the hedges, and pick up the trash.
Nantucket Boys and Girls Club: I sat on the board of directors here for nine years and chaired their summer benefit for three. （Fodder for my novel A Summer Affair!） The club is my number-one nonprofit because without a safe place for people to send their children after school, the island would stop running. The club underwent a massive renovation and it is now a leader among its peers—not only the building itself but the programming. If you donate to the club, you will be directly helping all of working Nantucket. Website: Nantucketboysandgirlsclub.org; Instagram: @nantucketbgc.
Nantucket Booster Club: All of our student athletes （among them three of my own children） have to travel on the fast ferry to get to away games. This costs money, as does ground transportation on the other side. If you’re a person who’s passionate about youth sports, then donating to the Boosters might be for you. Website: Nantucketboosterclub.com.