An idea to bring a little Christmas magic to a few children has turned into an annual campaign that has expanded to include hundreds of kids and help families in need.

It was during the pandemic that Anna Woosley came up with a festive plan to write letters from Santa to her nieces and nephews and children of family friends. The personalized letters were dressed up to look just like they came from the North Pole. They were stamped, placed in the mail and delivered to a few unsuspecting kids during the holiday season, much to their delight.

Anna, who moved from Kentucky to the Royal Hill subdivision in 2017, posted on Facebook about her small campaign and it was soon shared by several people who were drawn to the idea. By the next year, Anna’s workload had grown to 50 letters after receiving requests from both friends and strangers. By 2022, after additional social media response, the demand had grown even bigger.

“I’m from a small town, and when you post something on Facebook, it shares quickly,” said Anna, the mother of a third grader named Benji at Buffalo Ridge Elementary.

Anna dedicated her time and covered the costs of the stamps and decorative letters and envelopes because she said, “I wanted to alleviate something a mother might have on their task list, so they did not have to make their own letters or go through a third party.”

The project had grown so large by 2023 that she decided to turn it into a mechanism to give back. She collected voluntary contributions from the community via Venmo, and with each Santa letter included a coloring book and crayons for kids at Children’s Hospital Colorado and UK HealthCare at the University of Kentucky. A total of 795 letters went out that holiday season, including one to a friend’s daughter who was spending Christmas in the hospital and originally inspired the idea to include children with illnesses.

In 2024, Anna partnered with Healing Hurting Hearts in Denver and GreenHouse17 in Kentucky to send Santa letters to kids affected by gun violence. Last year, letters went to children in seven states; three single mothers in need each received $500.

Anna and Benji attend Flatirons Community Church in Denver every Sunday and enjoy watching the Denver Nuggets and University of Kentucky Wildcats teams. They also cook together regularly, travel to Disneyland and Disney World and are big fans of Harry Potter and Marvel movies.

When she was in fifth grade, Anna had gathered with a few friends and answered letters to Santa Claus written by the kindergartners and first graders at the school she attended. In the revived and slightly different model of what has become a seasonal passion project, Anna has been humbled by the responses from grateful parents and young recipients who got to experience an extra burst of joy during the holidays.

Deadline to ask Anna for letters is November 7. For more information, visit Anna’s Facebook page, facebook.com/anna.woosley.2025.

 

By Chris Michlewicz; photos courtesy of Anna Woosley