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Nantucket for the Holidays

Santa by Sea, Santa By Land

At a meeting on the Nantucket Christmas Stroll two years ago after the previous Santa retired, Tim Milstead says his manager at work thought of him immediately. “I have white hair and a white beard, and I’m a little heavier than I should be,” says Milstead, a Nantucket local and the director of engineering for Nantucket Island Resorts. This year, he and his wife are anticipating greeting upwards of 10,000 kids for their second year as Mr. and Mrs. Claus’s representatives at the Christmas Stroll. “It’s crazy,” Milstead said. “It’s so much fun. It’s the closest I’ll ever come to feeling like a rock star.”

Nantucket for the Holidays

On the Saturday of Stroll Weekend, December 1, a horse-drawn carriage delivers Milstead and his wife from the wharf where the Coast Guard drops the couple off, to the island’s Jared Coffin House where Milstead prepares for the biggest challenge of his role—answering children’s seemingly innocent questions. This can be daunting, Milstead says, because not only does he need to satisfy the children’s curiosity, but he also has to oblige their parents. It’s a good thing he’s had some practice – Milstead is a father of four himself.

“It’s amazing to see the excitement in their eyes,” Milstead says. “You kind of remember what it was like when you were little.” What Milstead says really thrills the kids is when Santa knows their names. They just can’t believe it, he says. The one question Milstead says children always ask him is, where are his reindeer? He’s settled on saying they are in the North Pole and they will come get him once he’s answered all of their questions.

Meet the Talking Tree

TJ Grant, a Nantucket Boys & Girls Club team coordinator and longtime Nantucket resident, has been the voice behind the enchanted Talking Christmas Tree for the past three years. Little do the children know, Grant looks out of the upstairs window at Pacific National Bank and a speaker system projects his voice down below while they wait to see Santa. All of the kids want to know how the tree can talk, Grant says, but what they care about most of all is how the tree knows their name! “It really blows them away,” he says. “It’s a lot of fun.” But Grant has to remind them, “You’re not going to get what you want for Christmas if you keep pulling my hair!” when they tear the tree’s pine needles out in their pursuit to find the source of the voice.

A Gifted Gallery

Nantucket for the Holidays

Defending doorway-decorating-contest champion and owner of The Gallery, Kathleen Knight looks forward to the competition every year. “It’s the only time of year I make art,” she says. Although she went to school for art, Knight buys and sells paintings to make a living. The contest is the one time of the year she expresses her own artistic creativity. The Gallery, located at 4 India Street, has won the doorway decorating contest every year since 2000. “I love Christmas. I’m a Christma-holic,” she says.

Even though the contest category was changed from doorway to storefront this year, Knight says, “I’ll still win it.” But she insists she doesn’t do it for the prizes. “I do it for the public,” she says. She loves to listen to patrons laughing outside her door, taking pictures with her creation. When asked what she has in store for this year, she wouldn’t budge an inch. One thing’s for sure, it’ll be the cat’s meow.

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Hillary Wenzel is a frequent contributor to Cape Cod Life

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