Santa is Busy Responding to His Rye Pen Pals

The “Dear Santa” program, organized by the Rye Recreation Department, lets kids share their wish lists, drawings, and holiday greetings with Santa using mailboxes on Purchase Street and at Rye Rec.
Photo by Alison Rodilosso

Hazel wants a hot pink digital clock. And a hot pink watch. And lots of friendship bracelets.

Her Christmas wish list, along with those of hundreds of other children in Rye and surrounding communities, was dropped off recently in one of the bright red mailboxes around town. Those boxes serve as Rye’s direct line to the North Pole — a beloved tradition that involves high school kids, too.

The “Dear Santa” program, organized by the Rye Recreation Department, lets kids share their wish lists, drawings, and holiday greetings with Santa using mailboxes on Purchase Street and at Rye Rec. This year, around 500 letters were mailed, said Anne Galletta, senior office assistant in the Rye High School Counseling Office.

In the past, many letters were mailed during the Mistletoe Magic festival, which was canceled this year. But children still mailed their letters, many decorated with stickers and crayon sketches. As in years past, those letters were sent not only from Rye, but also from Mamaroneck, Harrison, and Rye Brook.

At Rye High School, Santa’s helpers are hard at work helping their boss respond. One letter came from a boy who wants a Lego set as well as a “fire station” with “people and the tools with hoses.”

At the heart of the effort are Rye High School students, who volunteer as “honorary elves” to help Santa respond to every letter. Students earn community service hours for participating, though many return year after year, Galletta said.

“Even seniors who already have their community service hours done come back to help,” she said. “They really enjoy it.”

For Rye High School junior Darcy Lawrence, the program is an annual highlight.

“I may have taken about 10 more letters than I should have each day,” Lawrence said. “I absolutely loved doing it last year and loved it even more this year, especially because I babysit throughout Rye and recognize more names every year. That helps ‘Santa’ create a deeper connection with each child.”

Student volunteers are generally assigned four letters per day, though some take on additional letters when time allows. Despite juggling four AP classes and extracurriculars, Lawrence always makes time for writing letters.

“I know how much joy a child feels when they receive any letter in the mail — especially if it’s from Santa Claus,” she said. “Every year I look forward to this activity because I just absolutely love writing, and I love knowing that children will see their name in the mailbox and feel so happy that Santa responded to them.”

Jessie Watford, the assistant at Rye Rec who oversaw the program, said: “For me, the best part is mailing the responses back to the kids, and knowing it’s keeping the magic alive.”

Some of the letters are detailed wish lists with carefully pasted images, while others express their writers’ excitement for the Christmas season.

One letter, submitted by two brothers, also requested toys for their baby brother, who is too young to write a letter of his own.

“I noticed that all three of you have been exceptionally good this year — good job, boys,” Santa responded. “You always seem to be there for each other. No matter what, family is most important in life, and I see how much you value that.”

The high school volunteers carefully avoid promising specific gifts, and try to focus on kindness and values.

Running the program does come with some challenges. Some letters arrive without a return address, but usually Watford and the Rye Rec staff are able to track down missing addresses through their database.

Legibility, unsurprisingly, can create another roadblock.

“Sometimes we have to be detectives,” Lawrence said, noting that deciphering children’s handwriting can be tricky. “But it’s part of the fun.”

Despite the ease and pervasiveness of digital communication, Watford believes the tradition endures because of its simplicity and nostalgia.

“Digital may have its conveniences,” she said, “but there’s something truly special about analog and getting to hold a handwritten letter.”

Rye’s “Dear Santa” program serves as a reminder that holiday magic is very much a community effort.

Here’s hoping that Hazel gets her watch and her clock, as well as the last item on her wish list: “My parents happyness.”

Photos Courtesy of Rye City Schools

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